Water → HCID 14687817, compound

HRID 2198819Notes

Reaction equation

HRID 2198819 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:17].[BH4-].[Na+].O>C(O)(C)C>[OH:2][CH2:3][CH2:4][CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12249281HCID 12249281, compound

Product 1

HCID 14687817HCID 14687817, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

The crude ketoester (IX) from step 4 (approximately 180 gm; 0.7 mol) was refluxed for 8 hours with agitation under nitrogen with 74 gm (1.96 mol) of sodium borohydride in 1250 ml of isopropanol. After addition of 150 ml of water, the mixture was agitated for 30 minutes at 60° C., and any sodium borohydride remaining was destroyed by the addition of 100 ml of acetone with good cooling. After agitation for another 30 minutes, the isopropanol was distilled off with the simultaneous addition of 200 ml water. After cooling to approximately 30° to 35° C., the residue was neutralized with half-concentrated sulfuric acid and mixed with 700 ml of toluene. The aqueous phase was separated. The toluene phase contained approximately 135 gm of 1,4-diol (IV) (85% yield) and was used further without evaporation.

Workup

  1. customany sodium borohydride remaining was destroyed by the addition of 100 ml of acetone with good cooling
  2. waitAfter agitation for another 30 minutes
  3. distillationthe isopropanol was distilled off with the simultaneous addition of 200 ml water
  4. temperatureAfter cooling to approximately 30° to 35° C.
  5. additionmixed with 700 ml of toluene
  6. customThe aqueous phase was separated

Sources & evidence

ORD record
ord-c5f2e0713231436ca1cf13bf8a2eab0f
Source dataset
uspto-grants-1982_11
Patent number
US04360468

Reaction notes

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