Sodium borohydride → HCID 12656922, compound

HRID 1865754Notes

Reaction equation

HRID 1865754 reaction equation
[C:1]1([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[OH:13][CH:8]([C:7]([CH3:15])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:14])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44248134HCID 44248134, compound

Product 1

HCID 12656922HCID 12656922, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Following a procedure found in the literature (Ferguson, C. G.; Money, T.; Pontillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron. 52(47), 1996, 14661-14627) a solution of methyl 3-phenyl-3-methyl-2-oxobutanoate (2.5 g, 12 mmol, from Reference Example 36) in methanol (144 mL) is cooled to 0° C. (ice water bath). Sodium borohydride (0.21 g, 5.5 mmol) is added in three portions over 3 minutes. The reaction mixture is stirred at 0° C. for 10 minutes and then at room temperature for 30 minutes. The reaction mixture is quenched by the addition of 10% aqueous hydrochloric acid solution until pH=6 and then extracted thrice with diethyl ether. The combined extracts are washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfite, and concentrated under reduced pressure to give a light blond liquid, which is combined with the crude material from another reaction. The combined crude material is subjected to flash chromatography to (silica gel, hexanes/ethyl acetate) and provided 2.4 g (80% combined yield) of a clear, colorless oil. TOF MS (ES+): (M+H)=209.1

Workup

  1. waitat room temperature for 30 minutes
  2. customThe reaction mixture is quenched by the addition of 10% aqueous hydrochloric acid solution until pH=6
  3. extractionextracted thrice with diethyl ether
  4. washThe combined extracts are washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfite
  6. concentrationconcentrated under reduced pressure
  7. customto give a light blond liquid, which
  8. customprovided
  9. custom2.4 g (80% combined yield) of a clear, colorless oil

Sources & evidence

ORD record
ord-8a064fa20e7644a3aa892e398714f7dd
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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