Sodium borohydride → HCID 57890137, compound

HRID 1819939Notes

Reaction equation

HRID 1819939 reaction equation
[CH2:1]([C:3]([C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:14]([CH3:26])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[CH2:1]([C:3]([C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][CH:18]([OH:23])[C:19]([CH3:20])([CH3:22])[CH3:21])=[C:14]([CH3:26])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57890096HCID 57890096, compound

Product 1

HCID 57890137HCID 57890137, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of 1-{4-[1-Ethyl-1-(4-methyl-tliiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (5.2 g, 14 mmol) in THF/MeOH (40 ml/10 ml) at 0° C. is added NaBH4 (528 mg, 14 mmol), warmed to RT, and stirred for 1 h. The reaction is concentrated and the residue is partitioned between EtOAc and 0.2 N HCl. The organic layer is MgSO4 dried and concentrated to give the title compound (5.4 g, quantitative).

Workup

  1. concentrationThe reaction is concentrated
  2. customthe residue is partitioned between EtOAc and 0.2 N HCl
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea6f9c0cebaf4a25ac376a48846b918a
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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