Methanol → HCID 23071124, compound

HRID 1351944Notes

Reaction equation

HRID 1351944 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C:19](O)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CO>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][CH2:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 23071100[7-(Benzyloxy)-1H-indol-3-yl]acetic acid

Product 1

HCID 23071124HCID 23071124, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (7-(benzyloxy)-1H-indol-3-yl)acetic acid (7.21 g, 27.4 mmol) in tetrahydrofuran (150 mL) is added a 1M solution of borane.tetrahydrofuran complex in tetrahydrofuran (55 ml, 55 mmol) under nitrogen atmosphere, and the mixture is stirred at room temperature for 17 hours. To the reaction solution is added methanol (100 mL), and the mixture is stirred at room temperature for one hour. The solvent is evaporated, and the resulting crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1) to give 2-(7-(benzyloxy)-1H-indol-3-yl)ethanol (6.37 g, 23.8 mmol, yield: 87%).

Workup

  1. customThe solvent is evaporated
  2. customthe resulting crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-f5d2517793a142ec80393673df432e44
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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