[ CAS No. 1563-38-8 ]

Name: 1563-38-8|2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol|97%
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Quality Control of [ 1563-38-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1563-38-8 ]

CAS No. :	1563-38-8	MDL No. :	MFCD00075382
Formula :	C₁₀H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	164.20 g/mol	Pubchem ID :	15278
Synonyms :

Calculated chemistry of of [ 1563-38-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.46
TPSA :	29.46 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) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.67
Log Po/w (XLOGP3) :	2.08
Log Po/w (WLOGP) :	2.11
Log Po/w (MLOGP) :	1.71
Log Po/w (SILICOS-IT) :	2.48
Consensus Log Po/w :	2.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.54
Solubility :	0.475 mg/ml ; 0.00289 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	0.771 mg/ml ; 0.0047 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.223 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Safety of [ 1563-38-8 ]

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

Application In Synthesis of [ 1563-38-8 ]

* 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.

Downstream synthetic route of [ 1563-38-8 ]

[ 1563-38-8 ] Synthesis Path-Downstream 1~31

1
[ 1563-38-8 ]
[ 50893-53-3 ]
[ 101506-44-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With pyridine In dichloromethane for 5h; Ambient temperature;
84%	With pyridine In dichloromethane; water	23.a (a) (a) Synthesis of 1-chloroethyl 2,3-dihydro-2,2-dimethyl-7-benzofuranyl carbonate 21.5 g (0.15 mole) of 1-chloroethylchloroformate are added in a single portion to a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (24.6 g; 0.15 mole) in dichloromethane (150 ml). The mixture is cooled to between 0° and 5° C., and 12 g (0.15 mole) of pyridine are added dropwise. The mixture is stirred for 3 hours at 20° C. The organic phase is then washed with 2*50 ml of iced water. It is dried over magnesium sulphate and the solvent is evaporated. A yellow oil is obtained which is distilled. 34.1 g of the expected carbonate is then recovered (84% yield). B.p. 127° C./66.6 Pa (0.5 mm Hg).

Reference： [1]Barcelo, Gerard; Senet, Jean-Pierre; Sennyey, Gerard; Bensoam, Jean; Loffet, Albert [Synthesis, 1986, # 8, p. 627 - 632]
[2]Current Patent Assignee: AURELIUS SE & CO KGAA - US4725680, 1988, A

2
[ 1563-38-8 ]
[ 84428-21-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassiuim nitrosodisulfonate In ethanol; water at 20℃; for 1h;
84%	With potassium nitrososulfonate In ethanol; water for 0.166667h;	B.1 To a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (10.13 g, 61.7 mmol) in water/ethanol (7/3, 450 mL) was added potassium nitrosodisulfonate (Fremy 'USD salt, 48.26 g, 179 mmol) in seven portions. After stirring for additional 10 min, the reaction was diluted with water (-900 mL) and extracted with dichloromethane. The combined organic extracts were washed with water (400 mL), brine (400 mL), and concentrated in vacuo. Purification by flash chromatography afforded 2,2-dimethyl-2,3-dihydrobenzofuran-4,7-dione (9.23 g, 84%) as colorless oil.
	With potassiuim nitrosodisulfonate; sodium acetate; acetic acid In methanol; water at 25℃; for 1h;

3
[ 1563-38-8 ]
[ 22128-62-7 ]
[ 132905-88-5 ]

Yield	Reaction Conditions	Operation in experiment
73.5%	With sodium hydroxide; adogen 464 In water; benzene at 5℃; for 0.666667h;

Reference： [1]Patonay, Tamas; Patonay-Peli, Erzsebet; Mogyorodi, Ferenc [Synthetic Communications, 1990, vol. 20, # 18, p. 2865 - 2885]

4
[ 1563-38-8 ]
[ 106-95-6 ]
[ 87386-25-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate In acetone for 60h; Heating;

Reference： [1]Brown, Roger F.C.; Edwards, Gavin L.; Jones, Christopher M.; Rae, Ian D.; Teo, Peter Y. T. [Australian Journal of Chemistry, 1983, vol. 36, # 6, p. 1263 - 1273]

5
methallylpyrocatechol [ No CAS ]
[ 1563-38-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With iodine In dichloromethane for 0.5h; Ambient temperature;

Reference： [1]Kim, Kyoung Mahn; Ryu, Eung K. [Heterocycles, 1995, vol. 41, # 2, p. 219 - 224]

6
[ 1563-38-8 ]
[ 19810-32-3 ]
[ 222641-43-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine In benzene for 18h; Heating;

Reference： [1]Keserue, Gyoergy M.; Balogh, Gyoergy; Czudor, Iren; Karancsi, Tamas; Feher, Andras; Bertok, Bela [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 2, p. 762 - 769]

7
[ 1563-66-2 ]
[ 1563-38-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium hydroxide In ethanol
	With sodium hydroxide In water at 70℃; for 1h;	2.1. Reagents and solutions Solution 1.0 103 mol L-1 of carbofuran was prepared bydissolving 0.022 g of the compound in 100 mL solution of0.1 mol L1 NaOH which was heated for 1 hour in a temperatureof 70 C for the complete hydrolization of carbofuran tocarbofuran-phenol [32].

Reference： [1]Keserue, Gyoergy M.; Balogh, Gyoergy; Czudor, Iren; Karancsi, Tamas; Feher, Andras; Bertok, Bela [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 2, p. 762 - 769]
[2]Wong, Ademar; Materon, Elsa Maria; Sotomayor, Maria Del Pilar Taboada [Electrochimica Acta, 2014, vol. 146, p. 830 - 837]

8
[ 1563-38-8 ]
[ 358-23-6 ]
[ 308110-31-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine In dichloromethane at 20℃; for 1.5h;	15.1 Step 1: 2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate To a solution of 2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (190 µL, 1.27 mmol) and pyridine (206 µL, 2.55 mmol) in DCM (1.3 mL) at 0 °C was added triflic anhydride (287 µL, 1.56 mmol) in DCM (0.50 mL) dropwise. After complete addition, the mixture was warmed to room temperature and stirred for 1.5 hrs. The reaction was then diluted in EtOAc (10 mL) and washed with 1 N HCl (10 ml), NaHCO3 (aq) (10 mL) and brine (10 mL). The organic layer was dried with sodium sulfate and condensed to yield 2,2-dimethyl-2,3-dihydrobenzofuran-7-yl trifluoromethanesulfonate (380 mg, 1.28 mmol, 100% yield) as a yellow oil. 1H NMR (500 MHz, DMSO-d6) δ 7.28 (d, J = 7.4, 1.2 Hz, 1H), 7.21 (d, J = 8.3, 1.3 Hz, 1H), 6.91 (t, J = 8.4, 7.3 Hz, 1H), 3.13 (s, J = 1.1 Hz, 2H), 1.45 (s, 6H). 19F NMR (470 MHz, DMSO-d6) δ -73.44 (3F).
	With pyridine In dichloromethane at 25℃; for 1h;

Reference： [1]Current Patent Assignee: PRELUDE THERAPEUTICS INCORPORATED - WO2022/35799, 2022, A1 Location in patent: Paragraph 0310
[2]Plobeck; Delorme; Wei; Yang; Zhou; Schwarz; Gawell; Gagnon; Pelcman; Schmidt; Yue; Walpole; Brown; Zhou; Labare; Payza; St-Ogne; Kamassah; Morin; Projean; Ducharme; Roberts [Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894]

9
[ 1563-38-8 ]
[ 109-64-8 ]
[ 250289-95-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate; potassium iodide In acetone for 10h; Heating;

Reference： [1]Kossakowski, Jerzy; Hejchman, Elzbieta; Wolska, Irena [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2002, vol. 57, # 3, p. 286 - 294]

10
[ 1563-38-8 ]
[ 3132-64-7 ]
[ 250289-99-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate at 20℃; for 25h; Heating;

Reference： [1]Kossakowski, Jerzy; Hejchman, Elzbieta; Wolska, Irena [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2002, vol. 57, # 3, p. 286 - 294]

11
[ 1563-38-8 ]
4,6-dibromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-alcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bromine In chloroform at 20℃; for 1.5h;
83%	With bromine In chloroform at 0℃; for 1.5h;
67%	With bromine In chloroform at 25℃; for 2h;

67.3%	With bromine In chloroform at 0 - 20℃; for 2h;	2 Embodiment 2:4,6-dibromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-alcohol (V) of preparation [0088]Take 1g raw material 2,2-dimethyl -2,3-dihydrobenzofuran-7- alcohol(IV) (6.0mmol) in soluble to chloroform (35 ml) and reaches 0 °C slowly sloly instillment liquid bromine (1g, 15mmol, 2 . 5eq)Removed ice-bath afterreaction at room temperature 2 hours. concentration and removal of solventafter obtain brown solid,column chromatography (dichloromethane as eluant)after get the product 1.4g, the yield is 67.3%.
45%	With bromine In chloroform at 20℃; for 1.5h;

Reference： [1]Tapia, Ricardo A.; Alegria, Luz; Pessoa, Carlos D.; Salas, Cristian; Cortes, Manuel J.; Valderrama, Jaime A.; Sarciron, Marie-Elisabeth; Pautet, Felix; Walchshofer, Nadia; Fillion, Houda [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 10, p. 2175 - 2182]
[2]Sieveking, Ivan; Thomas, Pablo; Estevez, Juan C.; Quinones, Natalia; Cuellar, Mauricio A.; Villena, Juan; Espinosa-Bustos, Christian; Fierro, Angelica; Tapia, Ricardo A.; Maya, Juan D.; Lopez-Munoz, Rodrigo; Cassels, Bruce K.; Estevez, Ramon J.; Salas, Cristian O. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4609 - 4620]
[3]Jiang, Zhigan; Liu, Na; Dong, Guoqiang; Jiang, Yan; Liu, Yang; He, Xiaomeng; Huang, Yahui; He, Shipeng; Chen, Wei; Li, Zhengang; Yao, Jianzhong; Miao, Zhenyuan; Zhang, Wannian; Sheng, Chunquan [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4090 - 4094]
[4]Current Patent Assignee: SECOND MILITARY MEDICAL UNIVERSITY - CN103254191, 2016, B Location in patent: Paragraph 0087; 0088
[5]Vzquez, Karina; Espinosa-Bustos, Christian; Soto-Delgado, Jorge; Tapia, Ricardo A.; Varela, Javier; Birriel, Estefana; Segura, Rodrigo; Pizarro, Jaime; Cerecetto, Hugo; Gonzlez, Mercedes; Paulino, Margot; Salas, Cristian O. [RSC Advances, 2015, vol. 5, # 80, p. 65153 - 65166]

12
[ 1563-38-8 ]
[ 107-04-0 ]
[ 104392-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In butanone at 80℃; for 22h;
	With potassium iodide; sodium carbonate In dichloromethane; ethyl acetate	1 Preparation of 2,3-dihydro-2,2-dimethyl-7-(2'-chloro-ethoxy)-benzofuran EXAMPLE 1 Preparation of 2,3-dihydro-2,2-dimethyl-7-(2'-chloro-ethoxy)-benzofuran To 100 ml. ethylacetate 8.23 g. (0.05 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran, 14.3 g. (0.1 mole) 1-bromo-2-chloro-ethane, 6.9 g. (0.05 mole) anhydrous sodium carbonate and 8.3 (0.05 mole) potassium iodide are added. The reaction mixture is heated for 30 hours and the reaction is monitored by gas chromatographic analysis. When the reaction is completed the mixture is cooled to room temperature, the solid is removed by filtration and the solvent is distilled off in vacuo from the solvent layer on a rotatory film evaporator. The residual yellowish brown oily part is dissolved in 50 ml. methylene chloride and washed with 5*30 ml. 5% sodium-hydroxide solution and water. The solvent part is dried above anhydrous sodium sulphate and the solvent is distilled off on a rotatory film evaporator in vacuo. 5.8 g. yellowish brown liquid are obtained and purified by vacuo distillation. The product distilled at a pressure of 0.2 torr. at 120°-125° C.

13
[ 1563-38-8 ]
[ 132740-43-3 ]
2,2-dimethyl-2,3-dihydrobenzofuran-7-yl 4-fluorobenzylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In toluene Heating;

Reference： [1]Li, Weiwei; Blankman, Jacqueline L.; Cravatt, Benjamin F. [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9594 - 9595]

14
[ 1563-38-8 ]
[ 3173-53-3 ]
2,2-dimethyl-2,3-dihydrobenzofuran-7-yl cyclohexylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine In toluene Heating;

Reference： [1]Li, Weiwei; Blankman, Jacqueline L.; Cravatt, Benjamin F. [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9594 - 9595]

15
[ 1563-38-8 ]
[ 65535-53-7 ]
2,2-dimethyl-2,3-dihydrobenzofuran-7-yl 4-fluorophenethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine In toluene Heating;

Reference： [1]Li, Weiwei; Blankman, Jacqueline L.; Cravatt, Benjamin F. [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9594 - 9595]

16
[ 1563-38-8 ]
[ 54132-75-1 ]
2,2-dimethyl-2,3-dihydrobenzofuran-7-yl 3,5-dimethylphenylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In toluene Heating;

Reference： [1]Li, Weiwei; Blankman, Jacqueline L.; Cravatt, Benjamin F. [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9594 - 9595]

17
[ 1563-38-8 ]
[ 680203-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating 3: ethanolamine / 18 h / 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 48 h / 50 °C 2.1: potassium phtalimide; 18-crown-6 ether / N,N-dimethyl-formamide / 3 h / 50 °C 2.2: 2 h / 50 °C 2.3: 1 h / 20 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 48 h / 50 °C 2.1: 18-crown-6 ether / N,N-dimethyl-formamide / 3 h / 50 °C 3.1: methylamine / water / 2 h / 50 °C 3.2: 1 h / 20 °C

Reference： [1]Cuisiat, Stephane; Bourdiol, Nathalie; Lacharme, Vincent; Newman-Tancredi, Adrian; Colpaert, Francis; Vacher, Bernard [Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 865 - 876]
[2]Sniecikowska, Joanna; Gluch-Lutwin, Monika; Bucki, Adam; Wiȩckowska, Anna; Siwek, Agata; Jastrzebska-Wiesek, Magdalena; Partyka, Anna; Wilczyńska, Daria; Pytka, Karolina; Latacz, Gniewomir; Przejczowska-Pomierny, Katarzyna; Wyska, Elżbieta; Wesołowska, Anna; Pawłowski, Maciej; Newman-Tancredi, Adrian; Kolaczkowski, Marcin [Journal of Medicinal Chemistry, 2020, vol. 63, # 19, p. 10946 - 10971]
[3]Sniecikowska, Joanna; Gluch-Lutwin, Monika; Bucki, Adam; Wiȩckowska, Anna; Siwek, Agata; Jastrzebska-Wiesek, Magdalena; Partyka, Anna; Wilczyńska, Daria; Pytka, Karolina; Latacz, Gniewomir; Przejczowska-Pomierny, Katarzyna; Wyska, Elżbieta; Wesołowska, Anna; Pawłowski, Maciej; Newman-Tancredi, Adrian; Kolaczkowski, Marcin [Journal of Medicinal Chemistry, 2020, vol. 63, # 19, p. 10946 - 10971]

18
[ 1563-38-8 ]
[ 928403-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 48 h / 50 °C 2: 18-crown-6 ether / N,N-dimethyl-formamide / 3 h / 50 °C

19
[ 1563-38-8 ]
(5-cyclopent-1-enyl-pyridin-3-ylmethylene)-[2-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yloxy)-ethyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating 3: ethanolamine / 18 h / 20 °C 4: methanol / 15 h / 20 °C

20
[ 1563-38-8 ]
(3-cyclopent-1-enyl-benzylidene)-[2-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yloxy)-ethyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating 3: ethanolamine / 18 h / 20 °C 4: methanol / 15 h / 20 °C

21
[ 1563-38-8 ]
F₁₅₀₆₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating 3: ethanolamine / 18 h / 20 °C 4: methanol / 15 h / 20 °C 5: 7.35 g / KBH₄ / methanol / 4 h / 20 °C

22
[ 1563-38-8 ]
[2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl-oxy)ethyl]-(5-cyclopenten-1-ylpyridin-3-ylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: K₂CO₃ / butan-2-one / 22 h / 80 °C 2: 18 g / dimethylformamide / 2 h / Heating 3: ethanolamine / 18 h / 20 °C 4: methanol / 15 h / 20 °C 5: 1.17 g / KBH₄ / methanol / 4 h / 20 °C

23
[ 1563-38-8 ]
[ 583839-01-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 83 percent / bromine / CHCl₃ / 1.5 h / 20 °C 2: 51 percent / CrO₃; acetic acid / H₂O / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / 25 °C 2: chromium(VI) oxide / acetic acid; water / 1 h / 25 °C
	Multi-step reaction with 2 steps 1: bromine / chloroform / 1.5 h / 0 °C 2: chromium(VI) oxide; acetic acid / water / 1 h / 20 °C

	Multi-step reaction with 2 steps 1: bromine / chloroform / 1.5 h / 20 °C 2: chromium(VI) oxide; acetic acid / water / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / 0 - 20 °C 2: chromium(VI) oxide; acetic acid / water / 1 h

Reference： [1]Tapia, Ricardo A.; Alegria, Luz; Pessoa, Carlos D.; Salas, Cristian; Cortes, Manuel J.; Valderrama, Jaime A.; Sarciron, Marie-Elisabeth; Pautet, Felix; Walchshofer, Nadia; Fillion, Houda [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 10, p. 2175 - 2182]
[2]Jiang, Zhigan; Liu, Na; Dong, Guoqiang; Jiang, Yan; Liu, Yang; He, Xiaomeng; Huang, Yahui; He, Shipeng; Chen, Wei; Li, Zhengang; Yao, Jianzhong; Miao, Zhenyuan; Zhang, Wannian; Sheng, Chunquan [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4090 - 4094]
[3]Sieveking, Ivan; Thomas, Pablo; Estevez, Juan C.; Quinones, Natalia; Cuellar, Mauricio A.; Villena, Juan; Espinosa-Bustos, Christian; Fierro, Angelica; Tapia, Ricardo A.; Maya, Juan D.; Lopez-Munoz, Rodrigo; Cassels, Bruce K.; Estevez, Ramon J.; Salas, Cristian O. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4609 - 4620]
[4]Vzquez, Karina; Espinosa-Bustos, Christian; Soto-Delgado, Jorge; Tapia, Ricardo A.; Varela, Javier; Birriel, Estefana; Segura, Rodrigo; Pizarro, Jaime; Cerecetto, Hugo; Gonzlez, Mercedes; Paulino, Margot; Salas, Cristian O. [RSC Advances, 2015, vol. 5, # 80, p. 65153 - 65166]
[5]Current Patent Assignee: SECOND MILITARY MEDICAL UNIVERSITY - CN103254191, 2016, B

24
[ 1563-38-8 ]
[ 99517-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C

Reference： [1]Plobeck; Delorme; Wei; Yang; Zhou; Schwarz; Gawell; Gagnon; Pelcman; Schmidt; Yue; Walpole; Brown; Zhou; Labare; Payza; St-Ogne; Kamassah; Morin; Projean; Ducharme; Roberts [Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894]

25
[ 1563-38-8 ]
[ 38002-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C 3: DIBAl / toluene / 0.5 h / -78 °C 4: pyridinium dichromate / CH₂Cl₂ / 40 °C

26
[ 1563-38-8 ]
[ 38002-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C 3: DIBAl / toluene / 0.5 h / -78 °C

27
[ 1563-38-8 ]
[ 308110-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2.1: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C 3.1: DIBAl / toluene / 0.5 h / -78 °C 4.1: pyridinium dichromate / CH₂Cl₂ / 40 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 5.2: 67 percent / tetrahydrofuran; hexane / 1 h

28
[ 1563-38-8 ]
4-[chloro-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yl)-methyl]-<i>N</i>,<i>N</i>-diethyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2.1: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C 3.1: DIBAl / toluene / 0.5 h / -78 °C 4.1: pyridinium dichromate / CH₂Cl₂ / 40 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 5.2: 67 percent / tetrahydrofuran; hexane / 1 h 6.1: SOCl₂ / CH₂Cl₂ / 1 h / 25 °C

29
[ 1563-38-8 ]
[ 308110-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: pyridine / CH₂Cl₂ / 1 h / 25 °C 2.1: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C 3.1: DIBAl / toluene / 0.5 h / -78 °C 4.1: pyridinium dichromate / CH₂Cl₂ / 40 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 5.2: 67 percent / tetrahydrofuran; hexane / 1 h 6.1: SOCl₂ / CH₂Cl₂ / 1 h / 25 °C 7.1: 76 percent / acetonitrile / 12 h / 80 °C

30
[ 1563-38-8 ]
[ 1563-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 84 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature 2: 79 percent / aq. K₂CO₃ / tetrahydrofuran / 20 °C
	Multi-step reaction with 2 steps 1: 73.5 percent / Adogen 464, NaOH / benzene; H₂O / 0.67 h / 5 °C 2: 75.1 percent / Et₃N / petroleum ether; H₂O / 2.08 h / Ambient temperature
	In <i>N</i>,<i>N</i>-dimethyl-aniline	23.c (b) (c) The procedure is as in (a) followed by (b), but pyridine is replaced by N,N-dimethylaniline and the intermediate carbonate is not distilled. Starting with 16.4 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranol, 16.8 g (76%) of CARBOFURAN are then obtained, M.p. 147° C.

Reference： [1]Barcelo, Gerard; Senet, Jean-Pierre; Sennyey, Gerard; Bensoam, Jean; Loffet, Albert [Synthesis, 1986, # 8, p. 627 - 632]
[2]Patonay, Tamas; Patonay-Peli, Erzsebet; Mogyorodi, Ferenc [Synthetic Communications, 1990, vol. 20, # 18, p. 2865 - 2885]
[3]Current Patent Assignee: AURELIUS SE & CO KGAA - US4725680, 1988, A

31
[ 1563-38-8 ]
[ 530-62-1 ]
2,2-dimethyl-2,3-dihydrobenzo[2,3-b]benzofuran-7-yl imidazolecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 0.333333h;	4.o; 4.A Scheme 4; EXAMPLE 4; This example illustrates the preparation of N-{3-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propyl}(2,2-dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))-carboxamide (Compound 53 in table below); Step A Synthesis of 2,2-dimethyl-2,3-dihydrobenzo[2,3-b]benzofuran-7-yl imidazolecarboxylate as an Intermediate A solution of 1.64 grams (0.010 mole) of 2,2-dimethyl-2,3-dihydrobenzo[b]furan-7-ol (known compound) in 30 mL of methylene chloride was stirred, and 1.62 grams (0.010 mole) of 1,1'-carbonyldiimidazole was added in one portion. Upon completion of addition the reaction mixture was stirred at ambient temperature for 20 minutes. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in a mixture of 1:1 methylene chloride and hexanes and purified by column chromatography on silica gel using a mixture of 7:4 hexane and ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.96 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Reference： [1]Current Patent Assignee: FMC CORP - US2004/224994, 2004, A1 Location in patent: Page 8-9; 14

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[ CAS No. 1563-38-8 ]

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[ 1563-38-8 ] Synthesis Path-Downstream 1~31

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Alcohols

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Benzofurans

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[ 1563-38-8 ]

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