Hydrochloric Acid → [4-(2-Benzyloxycarbonyl-2-methylpropoxy)phenyl]methanol

HRID 2223599Notes

Reaction equation

HRID 2223599 reaction equation
[CH2:1]([O:8][C:9]([C:11]([CH3:23])([CH3:22])[CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>O1CCCC1>[CH2:1]([O:8][C:9]([C:11]([CH3:23])([CH3:22])[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:20][CH:21]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 230778534-(2-Benzyloxycarbonyl-2-methylpropoxy)benzaldehyde

Product 1

HCID 23077835[4-(2-Benzyloxycarbonyl-2-methylpropoxy)phenyl]methanolYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-benzyloxycarbonyl-2-methylpropoxy)benzaldehyde (0.97 g) in tetrahydrofuran (20 mL) was added sodium borohydride (59 mg), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-3/2) to give the title compound (0.95 g).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-3/2)

Sources & evidence

ORD record
ord-ba7620cc3c104216b6b4f33b9eb0cce2
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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