[ CAS No. 30595-79-0 ] {[proInfo.proName]}

Name: 30595-79-0|2,6-Dichlorophenethyl alcohol|98%
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Quality Control of [ 30595-79-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 30595-79-0 ]

CAS No. :	30595-79-0	MDL No. :	MFCD00800674
Formula :	C₈H₈Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZBQPKQUIKJDGIX-UHFFFAOYSA-N
M.W :	191.06	Pubchem ID :	2734100
Synonyms :

Calculated chemistry of [ 30595-79-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.4
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	3.03
Log Po/w (SILICOS-IT) :	3.27
Consensus Log Po/w :	2.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.179 mg/ml ; 0.000936 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.283 mg/ml ; 0.00148 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.026 mg/ml ; 0.000136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 30595-79-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 30595-79-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 30595-79-0 ]
Downstream synthetic route of [ 30595-79-0 ]

[ 30595-79-0 ] Synthesis Path-Upstream 1~5

1
[ 30595-79-0 ]
[ 118-69-4 ]
[ 28469-92-3 ]
[ 289058-20-4 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 21, p. 4011 - 4014

2
[ 6575-24-2 ]
[ 30595-79-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium aluminium tetrahydride In diethyl ether for 16 h; Heating / reflux	(vii) 2,6-Dichlorophenethyl alcohol: a suspension of lithium aluminum hydride (13.75 g, 365.75 mmol) in anhydrous diethyl ether (500 mL) was added via a powder addition funnel 2,6-dichlorophenylacetic acid (50 g, 243.75 mmol). The resulting reaction mixture was refluxed for 16 hours and then quenched by slow addition of a sodium sulfate saturated aqueous solution (25 mL). The resulting slurry was stirred for 3 hours and then filtered, the insoluble was carefully washed with diethyl ether (2 x 100 mL). The combined ether filtrates were dried over sodium sulfate and the solvent was evaporated in vacuo to yield 38.6 g (85percent yield) of the title compound.

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
[2] Patent: EP1087934, 2004, B1, . Location in patent: Page 28
[3] Journal of Medicinal Chemistry, 1970, vol. 13, # 6, p. 1051 - 1057
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 23, p. 5211 - 5217

3
[ 54551-83-6 ]
[ 30595-79-0 ]

Reference： [1] Patent: WO2009/87649, 2009, A1, . Location in patent: Page/Page column 23

4
[ 30595-79-0 ]
[ 230642-84-9 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 21, p. 4011 - 4014
[2] Tetrahedron Letters, 2000, vol. 41, # 21, p. 4011 - 4014
[3] Patent: WO2016/109359, 2016, A1,

5
[ 30595-79-0 ]
[ 209256-42-8 ]

Reference： [1] Patent: WO2016/109359, 2016, A1,
[2] Patent: CN106588841, 2017, A,

[ 30595-79-0 ] Synthesis Path-Downstream 1~58

1
[ 6575-24-2 ]
[ 30595-79-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium aluminium tetrahydride; In diethyl ether; for 16h;Heating / reflux;	(vii) 2,6-Dichlorophenethyl alcohol: a suspension of lithium aluminum hydride (13.75 g, 365.75 mmol) in anhydrous diethyl ether (500 mL) was added via a powder addition funnel 2,6-dichlorophenylacetic acid (50 g, 243.75 mmol). The resulting reaction mixture was refluxed for 16 hours and then quenched by slow addition of a sodium sulfate saturated aqueous solution (25 mL). The resulting slurry was stirred for 3 hours and then filtered, the insoluble was carefully washed with diethyl ether (2 x 100 mL). The combined ether filtrates were dried over sodium sulfate and the solvent was evaporated in vacuo to yield 38.6 g (85% yield) of the title compound.
73%	With borane; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	Under the protection of argon, Weigh compound 5-1 (5g, 24.4mmol) in anhydrous tetrahydrofuran (50mL), Cool down to 0 , Slowly add a 1M solution of borane in tetrahydrofuran (36.6mL, 36.6mmol), After the addition is complete, Warm to room temperature and stir overnight. After the reaction is complete, Slowly add water to quench the reaction, Transfer to a separatory funnel, Extracted with ethyl acetate (50mL x 3), Combined organic phases, Wash the organic phase with a saturated sodium bicarbonate solution (15 mL x 3) and saturated brine (15 mL x 3), Dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, Compound 5-2 was obtained without further purification (white solid, 3.40 g).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2818 - 2841
[2]Patent: EP1087934,2004,B1 .Location in patent: Page 28
[3]Patent: CN110627817,2019,A .Location in patent: Paragraph 0225-0228
[4]Journal of Medicinal Chemistry,1970,vol. 13,p. 1051 - 1057
[5]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

2
[ 30595-79-0 ]
[ 20973-90-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 0.5h;	Intermediate 43: (2,6-dichloro-phenyl)-acetaldehyde To a solution of <strong>[30595-79-0]2,6-dichlorophenylethylalcohol</strong> (2.0 g, 10.5 mmol) and CH2Cl2 (50 mL) was added acetic acid 1,1-diacetoxy-3-oxo-1lambda5-ioda-2-oxa-indan-1-yl ester (Dess-Martin periodinane; 4.9 g, 11.5 mmol) at rt. After 30 min. the mixture was diluted with satd. aq. NaHCO3 (10 mL) and satd. aq. Na2S2O3 (10 mL) and was stirred at rt for 1 h. The mixture was extracted with CH2Cl2 (3×15 mL) and the combined organic layers were dried (MgSO4), concentrated, and purified by FCC to afford a colorless solid (1.4 g, 70%). 1H NMR (CDCl3): 9.76 (dd, J=2.24, 1.12 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H). 7.25-7.20 (m, 1H), 4.14 (d, J=0.93 Hz, 1H).

Reference： [1]Patent: US2009/156599,2009,A1 .Location in patent: Page/Page column 18; 19
[2]Journal of Medicinal Chemistry,1970,vol. 13,p. 1051 - 1057

3
[ 30595-79-0 ]
[ 19564-42-2 ]

Reference： [1]Journal of Medicinal Chemistry,1970,vol. 13,p. 1051 - 1057

4
[ 30595-79-0 ]
[ 118-69-4 ]
[ 28469-92-3 ]
[ 289058-20-4 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 4011 - 4014

5
[ 30595-79-0 ]
[ 289058-20-4 ]

Yield	Reaction Conditions	Operation in experiment
99%		To a solution of 2-(2,6-dichlorophenyl)ethan- 1-ol (20 g, 104.68 mmol, 1.00 equiv) in pyridine (500 mL) was added sodium hydride (5.2 g,216.67 mmol, 1.25 equiv). The resulting solution was stirred at 0 C for 1 h. Then CuC1 (600 mg, 6.12 mmol, 0.05 equiv) was added. The resulting solution was stirred overnight at 115C. The resulting mixture was concentrated under vacuum. The reaction was then diluted with 500 mL of H20. The pH value of the solution was adjusted to 4 with HC1 (3 M). The solids were filtered out. The resulting solution was extracted with petroleum ether. And the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The cmde product was purified by 5i02 chromatography, eluted with petroleum ether to afford 16 g (99%) of 4-chloro-2,3-dihydro-1-benzofuran as colorless oil.
	With sodium hydride; copper(l) chloride; In tetrahydrofuran; ethyl acetate; at 70℃; for 18h;	Under nitrogen protection, 250 g2, 6-dichlorophenylethyl alcohol,6. 46 g of CuCl and 5.75 g of ethyl acetate with 7. 5 LTetrahydrofuran. Add 104.43 g NaH in batches while maintaining the temperature below 70 C. The resulting mixture was stirred at 70 C for 18 hours. The mass fraction of the starting material in the reaction system was controlled by gas chromatography <10%. The mixture was cooled to 5 to 10 C. Add 165 g of acetic acid while maintaining the temperature below 30 C. Add 1 L of water. The solvent is removed as far as possible at temperatures below 40 C. 2 L of heptane was added, and the resulting mixture was stirred for 10 minutes. After standing, the organic layer was separated and dried over MgSO4. The dried mixture was filtered and the filter cake was washed with 100 mL of heptane. The filtrates were combined and 80 g of silica gel was added to the combined filtrate. After sufficiently stirring, the filter was filtered and the filter cake was washed with 100 mL of heptane, and the filtrate was combined. Remove the solvent at 40 to 45 C. To obtain 220 g of an oil,4-chloro-2, 3-dihydrobenzofuran crude extract in a yield of 109% and a purity of 89%.
		Synthesis Example 20: Compound No.125 (2S,3R,4R,5S,6R)-2-(4-chloro-5-(chroman-6-ylmethyl)-2,3-dihydrobenzofuran-7-yl)-5-fluoro-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4-diol To a mixture of <strong>[30595-79-0]2-(2,6-dichlorophenyl)ethan-1-ol</strong> (200 g, 1.05 mol, 1.00 equiv) in toluene (3500 mL) was added NaH (52.8 g, 2.20 mol, 1.25 equiv, 60% purity). The mixture was stirred for 20 minutes at 40 C. To the resulting solution was then added CuCl (cuprous chloride) (5.21 g, 52.63 mmol, 0.05 equiv) and ethyl acetate (4.63 g, 52.61 mmol, 0.05 equiv). The reaction was stirred for overnight at reflux. Ice water was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SO4. The mixture was then concentrated and purified by chromatography on silica gel (50:1 PE/EA) to yield 4-chloro-2,3-dihydrobenzofuran as a yellow oil.

0.25 g

Under the protection of argon, Weigh compound 5-2 (0.5 g, 2.62 mmol) in anhydrous toluene (8 mL), Add sodium hydride (0.131 g, 3.28 mmol), After heating to 40 C and stirring for 15 minutes, Cool the reaction to room temperature, Cuprous chloride (13 mg, 0.131 mmol) was added, Toluene (2 mL) and ethyl acetate (0.013 mL) were subsequently added, Heated to 120 C and refluxed for 24h, After the reaction is completed, the reaction solution is cooled to room temperature. Slowly add ice water to quench the sodium hydride, filter to remove insoluble matter, The filtrate was diluted with water and transferred to a separating funnel. Extract with methyl tert-butyl ether (10 mL x 3), combine the organic phases, The organic phase was washed with saturated brine (5 mL x 3), dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 50: 1), Compound 5-3 (light yellow liquid, 0.25 g) was obtained.

Reference： [1]Patent: WO2016/109359,2016,A1 .Location in patent: Paragraph 00236
[2]Tetrahedron Letters,2000,vol. 41,p. 4011 - 4014
[3]Patent: CN106588841,2017,A .Location in patent: Paragraph 0054; 0055
[4]Patent: US2019/55226,2019,A1 .Location in patent: Paragraph 0534
[5]Patent: CN110627817,2019,A .Location in patent: Paragraph 0225; 0227; 0229

6
[ 30595-79-0 ]
[ 181472-07-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

7
C₁₀H₁₉NO₃S₂ [ No CAS ]
[ 30595-79-0 ]
(1R,2R)/(1S,2S)-1-(2,6-dichlorophenethoxy)-2-(3-thiazolidinyl)cyclohexane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2818 - 2841

8
C₁₁H₂₁NO₄S [ No CAS ]
[ 30595-79-0 ]
(1R,2R)/(1S,2S)-1-(2,6-dichlorophenethoxy)-2-(4-morpholinyl)cyclohexane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2818 - 2841

9
[ 30595-79-0 ]
[ 736971-27-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

10
[ 30595-79-0 ]
[ 871326-60-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

11
[ 30595-79-0 ]
[ 936946-50-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

12
[ 30595-79-0 ]
2-[2-(2,6-dichloro-phenyl)-ethyl]-thiazole-4-carboxylic acid (4-trifluoromethyl-phenyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

13
[ 30595-79-0 ]
[ 61698-06-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217

14
[ 30595-79-0 ]
[ 230642-84-9 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 4011 - 4014
[2]Tetrahedron Letters,2000,vol. 41,p. 4011 - 4014
[3]Patent: WO2016/109359,2016,A1

15
[ 30595-79-0 ]
[ 46398-59-8 ]

Reference： [1]Journal of Medicinal Chemistry,1970,vol. 13,p. 1051 - 1057

16
[ 30595-79-0 ]
[ 29096-65-9 ]

Reference： [1]Journal of Medicinal Chemistry,1970,vol. 13,p. 1051 - 1057

17
(1R,2R)/(1S,2S)-2-(1,4-Dioxa-7-azaspiro[4,4]non-7-yl)cyclohexanol [ No CAS ]
[ 30595-79-0 ]
(1R,2R)/(1S,2S)-2-[1,4-dioxa-7-azaspiro[4,4]non-7-yl]-1-(2,6-dichlorophenethoxy)cyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		(viii) To sodium hydride (144 mmol, 4.32 g, 80% oil dispersion) in anhydrous ethylene glycol dimethyl ether (80 mL) was added a solution of <strong>[30595-79-0]2,6-dichlorophenethyl alcohol</strong> (27.65 g, 144 mmol) in anhydrous ethylene glycol dimethyl ether (80 mL). The resulting mixture was stirred at room temperature under argon atmosphere for 4 hours.(ix) (1R,2R)/(1S,2S)-2-[1,4-Dioxa-7-azaspiro[4,4]non-7-yl]-1-(2,6-dichlorophenethoxy)cyclohexane: The mesylate (vi) in anhydrous ethylene glycol dimethyl ether (80 mL) was added quickly to the alkoxide mixture (viii) and the resulting mixture was readily refluxed for 66 hours. The cooled reaction mixture was poured into water (200 mL) and the organic solvent was evaporated in vacuo. The residual aqueous solution was diluted with more water to a volume of 700 mL, acidified to pH 0.5 with 6M HCI aqueous solution and extracted with diethyl ether (2 x 600 mL). The pH of the aqueous layer was adjusted to pH 5.9 and then the aqueous solution was extracted with diethyl ether (700 mL). The organic extract was dried over sodium sulfate and the solvent was evaporated in vacuo to yield 34.0 g of the title compound (70% yield).

Reference： [1]Patent: EP1087934,2004,B1 .Location in patent: Page 28

18
C₁₀H₁₉NO₃S₂ [ No CAS ]
[ 30595-79-0 ]
(1R,2R)/(1S,2S)-1-(2,6-dichlorophenethoxy)-2-(3-thiazolidinyl)cyclohexane monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(iii) To sodium hydride, 80% oil dispersion (608 mg, 20.28 mmol) in ethylene glycol dimethyl ether (30 mL) was added a solution of <strong>[30595-79-0]2,6-dichlorophenethyl alcohol</strong> (3.87 g, 20.28 mmol, example 4, step vii) in ethyleneglycol dimethyl ether (15 mL). The resulting mixture was stirred at room temperature under argon atmosphere for 2 hours. (iv) (1R,2R)/1S,2S)-2-(3-Thiazolidinyl)-1-(2,6-dichlorophenethoxy)cyclohexane monohydrochloride: The mesylate (ii) in ethylene glycol dimethyl ether (15 mL) was added quickly to the alkoxide (iii) and the reaction mixture was refluxed for 40 hours. The cooled reaction mixture was poured into water (100 mL) and the organic solvent was evaporated in vacuo. The residual aqueous solution was diluted with more water (100 mL) and the pH was adjusted to pH 1.5. The acidic aqueous solution was extracted with diethyl ether (3 x 100 mL), the combined organic extracts were dried over sodium sulfate and the solvent was removed in vacuo to provide the crude free base. The product was purified by dry-column chromatography with a mixture of ethyl acetate-hexanes (1:10, v/v) as eluent to yield 2.4 g of the crude free aminoether. The pure product (1.0 g) was converted to the hydrochloride salt by treatment with ethereal HCl and the resulting salt was recrystallized from a mixture of acetone-diethyl ether to yield 0.69 g of the title compound, having the elemental analysis indicated in Table 1.

Reference： [1]Patent: EP1087934,2004,B1 .Location in patent: Page 30

19
[ 54551-83-6 ]
[ 30595-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In tetrahydrofuran; water; at 5 - 10℃; for 4h;	2,6-Dichloro phenyl acetic acid methyl ester (1 eq) was taken in THF: Water (10:0.1(v/v) and cooled to 5-10 0C. NaBH4 was added to this mixture and mixture was stirred for 4 h. Mixture was quenched in water and extracted with EtOAc. Organic layer was washed with brine and evaporated in vacuo to afford title compound as thick liquid.

Reference： [1]Patent: WO2009/87649,2009,A1 .Location in patent: Page/Page column 23

20
[ 30595-79-0 ]
(E)-3-(4-methoxy-2-oxo-2H-pyran-6-yl)acrylic acid [ No CAS ]
(E)-2,6-dichlorophenethyl 3-(4-methoxy-2-oxo-2Hpyran-6-yl)acrylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4714 - 4726

21
[ 30595-79-0 ]
methyl 5-cyclopropyl-3-(2,6-dichlorophenethyl)-2-oxo-2,3-dihydrooxazole-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/96116,2016,A1
[2]Patent: WO2016/96115,2016,A1

22
[ 30595-79-0 ]
5-cyclopropyl-3-(2,6-dichlorophenethyl)-4-(hydroxymethyl)oxazol-2(3H)-one [ No CAS ]

Reference： [1]Patent: WO2016/96116,2016,A1
[2]Patent: WO2016/96115,2016,A1

23
[ 30595-79-0 ]
[ 124-63-0 ]
2,6-dichlorophenethyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	Step3: 2,6-dichlorophenethyl methanesulfonate (38c) To a solution of <strong>[30595-79-0]2-(2,6-dichlorophenyl)ethanol</strong> (37.3 g, 195 mmol) and TEA (32.7 g, 235 mmol) in DCM (700 mL) was added MsCI (26.9 g, 235 mmol) dropwise at 0C. After addition, the solution was stirred at rt overnight, diluted with water (200 mL) and extracted with DCM (3 x 400 mL). The combined organic layer was dried over Na2S04, filtered, concentrated and purified by flash chromatography (PE/EtOAc = 5:1 ) to afford 2,6-dichlorophenethyl methanesulfonate 38c. H-NMR (300 MHz, CDCI3): delta 2.95 (s, 3H), 3.43 (t, J = 7.5 Hz, 2H), 4.41 (t, J = 7.5 Hz, 2H), 7.12-7.17 (m, 1 H), 7.31 (d, J = 8.4 Hz, 2H).
	With triethylamine; In dichloromethane; at 0 - 20℃;	Step 3: To a solution of <strong>[30595-79-0]2-(2,6-dichlorophenyl)ethanol</strong> (37.3 g, 195 mmol) and TEA (32.7 g, 235 mmol) in DCM (700 mL) was added MsCI (26.9 g, 235 mmol) dropwise at 0C. After addition, the solution was stirred at rt overnight, diluted with water (200 mL) and extracted with DCM (3 x 400 mL). The combined organic layer was dried over Na2S04, filtered, concentrated and purified by flash chromatography (PE/EtOAc = 5:1 ) to afford 2,6-dichlorophenethyl methanesulfonate lnt-1 c- 11. 1H-NMPi (300 MHz, CDCI3): delta 2.95 (s, 3H), 3.43 (t, J = 7.5 Hz, 2H), 4.41 (t, J = 7.5 Hz, 2H), 7.12-7.17 (m, 1 H), 7.31 (d, J = 8.4 Hz, 2H)

Reference： [1]Patent: WO2016/96116,2016,A1 .Location in patent: Page/Page column 65-66
[2]Patent: WO2016/96115,2016,A1 .Location in patent: Page/Page column 39

24
[ 30595-79-0 ]
(Z)-N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methylidene]hydroxylamine [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

25
[ 30595-79-0 ]
1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1
[2]Patent: CN106588841,2017,A

26
[ 30595-79-0 ]
[ 609799-22-6 ]

Reference： [1]Patent: WO2016/109359,2016,A1
[2]Patent: CN106588841,2017,A

27
[ 30595-79-0 ]
[ 209256-42-8 ]

Reference： [1]Patent: WO2016/109359,2016,A1
[2]Patent: CN106588841,2017,A

28
[ 30595-79-0 ]
[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl](²H)formaldehyde [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

29
[ 30595-79-0 ]
(Z)-N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl](²H)methylidene]hydroxylamine [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

30
[ 30595-79-0 ]
[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl](²H₂)methanamine [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

31
[ 30595-79-0 ]
N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl](²H₂)methyl]propanamide [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

32
[ 30595-79-0 ]
[ 209256-69-9 ]

Reference： [1]Patent: WO2016/109359,2016,A1

33
[ 30595-79-0 ]
(2E)-3-(2,3-dihydro-1-benzofuran-4-yl)-N-methoxyprop-2-enamide [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

34
[ 30595-79-0 ]
(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)-N-methoxy-N-methylcyclopropane-1-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1

35
[ 30595-79-0 ]
(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carbaldehyde [ No CAS ]

Reference： [1]Patent: WO2016/109359,2016,A1
[2]Patent: CN106588841,2017,A

36
[ 30595-79-0 ]
(1R-trans)-2-(2,3-dihydro-4-benzofuranyl)cyclopropanecarboxylic acid [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

37
[ 30595-79-0 ]
(1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropanemethanol [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

38
[ 30595-79-0 ]
3-(2,3-dihydrobenzofuran-4-yl)prop-2-enoic acid [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

39
[ 30595-79-0 ]
C₂₁H₂₅NO₄S [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

40
[ 30595-79-0 ]
C₂₂H₂₇NO₄S [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

41
[ 30595-79-0 ]
C₁₃H₁₄O₃ [ No CAS ]

Reference： [1]Patent: CN106588841,2017,A

42
[ 30595-79-0 ]
methyl 1-(7-hydroxychroman-3-yl)azetidine-3-carboxylate [ No CAS ]
methyl 1-(7-(2,6-dichlorophenethoxy)chroman-3-yl)azetidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 mg		69.1 Methyl 1-(7-(2,6-dichlorophenethoxy)chroman-3-yl)azetidine-3-carboxylate Triphenylphosphine (125 mg, 0.475 mmol) was added to a solution of methyl 1-(7-hydroxychroman-3-yl)azetidine-3-carboxylate (50 mg, 0.19 mmol) with <strong>[30595-79-0]2-(2,6-dichlorophenyl)ethanol</strong> (54.4 mg, 0.285 mmol) in DCM and stirred for 30 minutes. (E)-Diisopropyl diazene-1,2-dicarboxylate (DIAD, 96 mg, 0,475 mmol) was added drop wise and the mixture was stirred overnight. Then the mixture was concentrated and the residue dissolved in ethyl acetate and sat. NaHCO3, The organic phase was dried (Na2SO4), filtered, evaporated and the crude purified by chromatography (silica gel) affording 80 mg of the desired product as clear oil.

Reference： [1]Patent: US2017/174672,2017,A1 .Location in patent: Paragraph 0952

43
[ 30595-79-0 ]
5-bromo-4-chloro-2,3-dihydrobenzofuran [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

44
[ 30595-79-0 ]
4-chloro-2,3-dihydrobenzofuran-5-carbaldehyde [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

45
[ 30595-79-0 ]
(2S,3R,4R,5S,6R)-2-(4-chloro-5-(chroman-6-ylmethyl)-2,3-dihydrobenzofuran-7-yl)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

46
[ 30595-79-0 ]
7-bromo-4-chloro-2,3-dihydrobenzofuran-5-carbaldehyde [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

47
[ 30595-79-0 ]
(7-bromo-4-chloro-2,3-dihydrobenzofuran-5-yl)(chroman-6-yl)methanol [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

48
[ 30595-79-0 ]
6-((7-bromo-4-chloro-2,3-dihydrobenzofuran-5-yl)methyl)chromane [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

49
[ 30595-79-0 ]
(3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(4-chloro-5-(chroman-6-ylmethyl)-2,3-dihydrobenzofuran-7-yl)-5-fluorotetrahydro-2H-pyran-2-ol [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

50
[ 30595-79-0 ]
6-((7-((2S,3S,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluorotetrahydro-2H-pyran-2-yl)-4-chloro-2,3-dihydrobenzofuran-5-yl)methyl)chromane [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

51
[ 30595-79-0 ]
C₁₄H₁₉BO₃ [ No CAS ]