Hydrochloric Acid → HCID 178445063, compound

HRID 635135

Reaction equation

HRID 635135 reaction equation
[CH2:1]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH3:5].[BH4-].[Na+].Cl>CO.CCOCC>[CH2:3]([O:26][C@H:23]1[CH2:24][CH2:25][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([C:9]34[CH2:8][CH2:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])([CH2:11][CH2:10]3)[CH2:13][CH2:12]4)=[CH:15][CH:16]=2)[CH2:21][CH2:22]1)/[CH:2]=[CH:1]/[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 212577934-[4-(4-Pentylbicyclo[2.2.2]octyl)phenyl]cyclohexanone

Product 1

HCID 178445063HCID 178445063, compoundYield 127.8%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent2×

Procedure

4-[4-(4-pentylbicyclo[2.2.2]octyl)penyl]cyclohexanone (1.5 g, 4.3 mmol) and a mixture of 9:1 methanol/ether (25 cm3) is added dropwise to a freshly prepared mixture of sodium borohydride (1.2 g, 8.5 mmol) and a mixture of 9:1 methanol/ether (25 cm3) at 0° C. When the addition is complete, the reaction mixture is stirred overnight at room temperature. A 25 per cent hydrochloric acid solution is added carefully to the reaction mixture, which was extracted into ethyl acetate (3×50 cm3). The combined organic extracts are washed with water (2×500 ml) and dilute sodium carbonate solution (2×500 ml), dried (MgSO4), filtered and then evaporated down. The residue is purified by column chromatography on silica gel using a 7:3 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield the pure 1-[4-(trans-4-hydroxycyclohexyl)phenyl]-4-pentylbicyclo[2.2.2]octane (1.2 g, 80 per cent).

Workup

  1. additionWhen the addition
  2. extractionwas extracted into ethyl acetate (3×50 cm3)
  3. washThe combined organic extracts are washed with water (2×500 ml) and dilute sodium carbonate solution (2×500 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue is purified by column chromatography on silica gel using a 7:3 hexane/ethyl acetate mixture as eluent
  8. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-564794c6b29c4c3f9f1bf2930b933a9b
Source dataset
uspto-grants-2001_02
Patent number
US06187393B1

Linked notes

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