Hydrochloric Acid → [2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanol

HRID 1766649Notes

Reaction equation

HRID 1766649 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:15][C:12]=1[CH:13]=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.Cl>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:15][C:12]=1[CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 23031138HCID 23031138, compound

Product 1

HCID 23031098[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanolYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium borohydride (340 mg) in tetrahydrofuran (10 mL) was added 2-benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde (3.30 g) under ice-cooling. After adding dropwise methanol (1 mL) at room temperature, the mixture was stirred for 6 hours. The reaction mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (3.13 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0a9ec01159d747c09d87d6de3cd7bb54
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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