Acetic Acid → HCID 54100099, compound

HRID 483651Notes

Reaction equation

HRID 483651 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[CH2:7][CH:8]=[C:9]([F:15])[CH2:10][CH2:11][CH2:12][CH:13]=[O:14].[BH4-].[Na+].CC(C)=O.C(O)(=O)C>CO>[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[CH2:7][CH:8]=[C:9]([F:15])[CH2:10][CH2:11][CH2:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 53880984HCID 53880984, compound

Product 1

HCID 54100099HCID 54100099, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The aldehyde prepared in 2G (0.937 g, 3.77 mmoles) was dissolved in methanol (20 ml) and cooled to 0° C. Sodium borohydride (0.071 g, 1.87 mmoles) was added and the mixture was stirred 30 min. Acetone was added to react with an excess of sodium borohydride and then the reaction mixture was acidified with acetic acid. The solvents were evaporated under reduced pressure. The residue was diluted with ether and washed with water. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title alcohol as an oil in a quantitative yield. NMR (H1, CDCl3, 60MHz) characteristic peaks 4 (t, JHH =7 Hz, 1), 5.1 (dt, JHF =21 Hz, JHH =8 Hz, 1).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. additionThe residue was diluted with ether
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15c95475b9ba45779a6a929d2a2d8b7e
Source dataset
uspto-grants-1993_07
Patent number
US05225429

Reaction notes

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