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

HRID 844793Notes

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-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 concentrated under reduced pressure. The title compound was isolated by column chromatography (5-10% EtOAc-hexanes) as a colorless oil, 355.0 mg (90%).

Workup

customcarefully quenched with H2O
extractionextracted with Et2O
washThe combined organic layers were washed with H2O and saturated aqueous NaCl
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8dc28d3f6cd74cbcbbee84822591f294
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380256B1

Reaction notes

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