Sodium borohydride → 4-Hydroxymethyl-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate

HRID 1597028Notes

Reaction equation

HRID 1597028 reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=[O:5])=[O:4].[BH4-].[Na+]>CO>[F:18][C:2]([F:1])([F:19])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 225689104-Formyl-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate2×

Product 1

HCID 225688934-Hydroxymethyl-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-formyl-3-isopropyl-phenyl 1,1,1-trifluoro-methansulfonate (Intermediate 148, 540.0 mg, 1.82 mmols) in 7 mL MeOH at 0° C. was added NaBH4 (72.0 mg, 1.91 mmols). After stirring 2 hours at 0° C. the reaction was carefully quenched with H2O and extracted with Et2O. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concetrated under reduced pressure. The title compound was isolated by column chromatography (5-10% EtOAc-hexanes) as a colorless oil, 355.0 mg (90%).

Workup

  1. customwas carefully quenched with H2O
  2. extractionextracted with Et2O
  3. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e210215499be4dd7a822af90c07a4e5d
Source dataset
uspto-grants-2001_09
Patent number
US06291677B1

Reaction notes

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