Hexane → 1-Benzyloxycarbonyl-5-chloro-3-hydroxymethylindole

HRID 564847Notes

Reaction equation

HRID 564847 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([CH:21]=[O:22])=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+].CCCCCC>CO>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([CH2:21][OH:22])=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 184739871-Benzyloxycarbonyl-5-chloro-3-formylindol

Product 1

HCID 184739211-Benzyloxycarbonyl-5-chloro-3-hydroxymethylindoleYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyloxycarbonyl-5-chloro-3-formylindol (2.00 g) in methanol (13 ml) was added sodium borohydride (241 mg) at 0° C. After the mixture was stirred for 15 minutes at the same temperature, ice water was added to the mixture. Potassium carbonate was added to make the mixture saturate. The whole was extracted with ether and the extract was dried over magnesium sulfate. Concentration of the mixture gave a residue, to which hexane was added. 1-benzyloxycarbonyl-5-chloro-3-hydroxymethylindol (1.80 g) was obtained as a crystal.

Workup

  1. additionwas added to the mixture
  2. concentrationsaturate
  3. extractionThe whole was extracted with ether
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customConcentration of the mixture gave a residue

Sources & evidence

ORD record
ord-898dfe3616994e3ab98882b6312c6e7d
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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