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

HRID 51812Notes

Reaction equation

HRID 51812 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-methanesulfonate (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-7a1a9ad13f054ca7ab1f81b1be6ac8a2
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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