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

HRID 395200Notes

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

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

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

Sources & evidence

ORD record: ord-3b54acb0c06a4fb09750cfb9fc63b712
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603019B2

Reaction notes

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