Water → HCID 23371774, compound

HRID 1899862Notes

Reaction equation

HRID 1899862 reaction equation
[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7](=[O:13])[C:6]=2[CH:14]=1.[BH4-].[Na+].O>C(O)C>[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH:7]([OH:13])[C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23371776HCID 23371776, compound

Product 1

HCID 23371774HCID 23371774, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of the product of step c (26.9 g) in C2H5OH (200 ml) at 5° C. is treated with sodium borohydride (1.95 g) and stirred at room temperature for 12 h. The solvent is evaporated off under reduced pressure to give a residue which is treated with H2O (500 ml) and extracted with diethyl ether (3×200 ml). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product. This is purified by chromatography (silica gel, 10% acetone in hexane) and recrystallized from diethyl ether-pentane to give the title compound, m.p. 92°-93° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customto give a residue which
  3. extractionextracted with diethyl ether (3×200 ml)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customto yield the crude product
  8. customThis is purified by chromatography (silica gel, 10% acetone in hexane)
  9. customrecrystallized from diethyl ether-pentane

Sources & evidence

ORD record
ord-0767503eee6c40b9a91cce9df1046105
Source dataset
uspto-grants-1996_11
Patent number
US05574049

Reaction notes

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