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

HRID 427957
Notes
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Reaction equation

HRID 427957 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 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

  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)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-013f11117feb4a5799dcbaa3510c3c8b
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313107B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes