Sodium borohydride → HCID 178521563, compound

HRID 1463748Notes

Reaction equation

HRID 1463748 reaction equation
[BH4-].[Na+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[CH2:12][CH2:11]1>C(O)(C)C.Cl>[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[CH2:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]2)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178516051HCID 178516051, compound

Product 1

HCID 178521563HCID 178521563, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent2×

Procedure

A suspension of 2.97 g of sodium borohydride in 300 ml of isopropanol was treated dropwise while gassing with nitrogen at -70° C. with a solution of 11 g of 4-[trans-4-[2-(1,3-dioxolan-2-yl) ethyl]cyclohexyl]cyclohexanone in 200 ml of isopropanol. After about 1 hour the reaction mixture was left to warm to room temperature, diluted with 500 ml of 0.1N hydrochloric acid and extracted three times with 300 ml of methylene chloride each time. The organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. Crystallization of the residue (11 g) from 500 ml of ethyl acetate/petroleum ether (vol. 3:5) gave 6.6 g of pure trans-4-[trans-4-[2-(1,3-dioxolan-2-yl) ethyl]cyclohexyl]cyclohexanol with m.p. 129.5° C.

Workup

  1. additionwas treated dropwise
  2. extractionextracted three times with 300 ml of methylene chloride each time
  3. washThe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customCrystallization of the residue (11 g) from 500 ml of ethyl acetate/petroleum ether (vol. 3:5)

Sources & evidence

ORD record
ord-75a639c275804d5097938334ed82e9dc
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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