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[ CAS No. 274910-19-9 ]

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2D
Chemical Structure| 274910-19-9
Chemical Structure| 274910-19-9
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Product Details of [ 274910-19-9 ]

CAS No. :274910-19-9MDL No. :MFCD03659696
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :166.17Pubchem ID :2776182
Synonyms :

Computed Properties of [ 274910-19-9 ]

TPSA : 38.7 H-Bond Acceptor Count : 3
XLogP3 : 0.8 H-Bond Donor Count : 1
SP3 : 0.33 Rotatable Bond Count : 1

Safety of [ 274910-19-9 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 274910-19-9 ]

  • Upstream synthesis route of [ 274910-19-9 ]
  • Downstream synthetic route of [ 274910-19-9 ]

[ 274910-19-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 274910-19-9 ]
  • [ 214894-89-0 ]
YieldReaction ConditionsOperation in experiment
62% With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1.16667 h; A solution of 20 (3.75 g, 32.3 mmol) in diethyl ether (80 mL) was cooled to 0 °C and phosphorous tribromide (3.67 mL, 38.8 mmol) was added dropwise. The solution was stirred at 0 °C for 10 min, then at r.t. for 1 h. Water (10 mL) was added cautiously to quench the excess of reagent and the mixture was diluted with diethyl ether and washed with water (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 21 as a brown solid (4.61 g, 62percent). 1H NMR (CDCI3) δ 6.91-6.77 (m, 3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found: [M+H- Br]=149.5.
62% With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1 h; A solution of the above alcohol (3.75 g, 32.3 mmol) in Et2O (80mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8mmol) was added dropwise. The solution was stirred at 0 C for 10min, then at 20 C for 1 h. Water (10 mL) was added cautiously toquench the excess of reagent and the mixture was diluted withdiethyl ether and washed with water (3 50 mL). The combinedorganic layers were washed with brine (100 mL), dried over Na2-SO4, filtered and concentrated under reduced pressure to obtain5-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine as a brownsolid (4.61 g, 62percent). 1H NMR (CDCl3, 400 MHz) d 6.91–6.77 (m,3H), 4.52 (s, 2H), 4.35–4.33 (m, 2H), 4.29–4.27 (m, 2H). Found:[M+H-Br] = 149.5.
Reference: [1] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0076
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
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  • [ 4442-53-9 ]
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YieldReaction ConditionsOperation in experiment
99% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18 h; To a solution of 2,3-dihydrobenzo[£][l,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol) in THF (150 mL) at 0 °C was added lithium aluminium hydride (2.13 g, 56.0 mmol) in small portions. The reaction mixture was stirred at 0 °C for 10 min and stirred for a further 18 h at r.t. Water (150 mL) was added to the reaction mixture which was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 20 as yellow oil (3.22 g, 99percent). 1H NMR (CDC13) δ 6.87-6.79 (m, 3H), 4.66 (s, 2H), 4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18]=149.5
99% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18 h; 4.1.1.1. 6-Bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methyl)-2-methoxyquinoline (VI: Y = 2,3-O(CH2)2O–). To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol)in THF (150 mL) at 0 C was added lithium aluminium hydride(2.13 g, 56.0 mmol) in small portions. The reaction mixture wasstirred at 0 C for 10 min and stirred for a further 18 h at 20 C.Water (150 mL) was added to the reaction mixture which wasextracted with EtOAc (2 100 mL). The combined organic layerswere washed with brine (100 mL), dried over Na2SO4, filteredand concentrated under reduced pressure to obtain (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol as a yellow oil (3.22 g,99percent). 1H NMR (CDCl3, 400 MHz) d 6.87–6.79 (m, 3H), 4.66 (s, 2H),4.32–4.30 (m, 2H), 4.28–4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18] = 149.5.
Reference: [1] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0075
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 3
  • [ 29668-43-7 ]
  • [ 274910-19-9 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 803 - 807
[2] Patent: US5122523, 1992, A,
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  • [ 261767-10-6 ]
  • [ 274910-19-9 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In diethyl ether; water Example 5
5-hydroxymethyl-1,4-benzodioxan (5).
To a suspension of lithium aluminum hydride (7.0 g, 0.18 mmol) in dry diethyl ether (100 mL) was added a solution of ethyl 1,4-benzodioxan-5-carboxylate (35 g, 0.17 mmol) in diethyl ether (100 mL).
After boiling under reflux for 2 h, the reaction mixture was cooled to 0° C. and carefully treated with water (35 mL) and 4N aqueous sodium hydroxide (35 mL).
The resulting mixture was filtered and dried (Na2SO4).
Evaporation of the solvents afforded 25 g (88percent) crystalline title compound: mp 51-53° C.; 1H NMR (CDCl3) δ 2.50 (s, 1H), 4.20-4.3 (m, 4H), 4.60 (s, 2H), 6.75-6.90 (m, 3H).
Reference: [1] Patent: US2002/32205, 2002, A1,
  • 5
  • [ 24677-78-9 ]
  • [ 106-93-4 ]
  • [ 274910-19-9 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: With caesium carbonate In DMF (N,N-dimethyl-formamide) for 2 h; Heating / reflux
Stage #2: With sodium tetrahydroborate In DMF (N,N-dimethyl-formamide); ethanol at 20℃; for 1 h;
Preparation 87; (2,3-Dihydrobenzo [1, 4] dioxin-5-yl) acetonitrile; (2, 3-Dihydrobenzorl, 41dioxin-5-yl) methanol; Dissolve 2,3-Dihydroxybenzaldehyde (25 g, 181 mmol) and 1,2-dibromoethane (34 g, 181 mmol) in N, N-dimethylformamide (500 mL). Add cesium carbonate (118 g, 362 mmol), stir and reflux under nitrogen for 2 hours. Cool the reaction to 20°C, dilute with absolute ethanol (250 mL) and add sodium borohydride (6.8 g, 181 mmol). Stir at 20°C for 1 hour and concentrate under high vacuum to remove the ethanol and dimethylformamide. Dilute the residue with diethyl ether and wash with distilled water, 0.25 molar aqueous sodium hydroxide, and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from 75percent hexane, 25percent ethyl acetate to 25percent hexane, 75percent ethyl acetate to obtain the title compound as a white solid. HRMS : 166.0621 (M); Preparation 129; 2- (2, 3-Dihydrobenzo [1, 4] dioxin-5-yl) acetamide; (2, 3-Dihydrobenzo f 1, 41 dioxin-5-yl) methanol; Dissolve 2,3-dihydroxybenzaldehyde (25 g, 181 mmol) and 1,2-dibromoethane (34 g, 181 mmol) in N, N-dimethylformamide (500 mL). Add cesium carbonate (118 g, 362 mmol), stir and reflux under nitrogen for 2 hours. Cool the reaction to 20°C, dilute with absolute ethanol (250 mL) and add sodium borohydride (6.8 g, 181 mmol). Stir at 20°C for 1 hour and concentrate under high vacuum to remove the ethanol and dimethylformamide. Dilute the residue with diethyl ether and wash with distilled water, 0.25 molar aqueous sodium hydroxide, and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from 75percent hexane, 25percent ethyl acetate to 25percent hexane, 75percent ethyl acetate to obtain 8. 1 g (27percent) of the desired compound as a white solid. HRMS: m/z = 166.0621 (M)
Reference: [1] Patent: WO2003/76442, 2003, A1, . Location in patent: Page/Page column 49; 63-64
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  • [ 274910-19-9 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 803 - 807
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