Methanol → HCID 178444111, compound

HRID 254125Notes

Reaction equation

HRID 254125 reaction equation
[C:1]([CH:3]([C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]1)[CH2:4][CH2:5][C:6](=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])#[N:2].CO.[BH4-].[Na+]>C1COCC1.O>[C:1]([CH:3]([C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][CH3:21])[CH2:16][CH2:15]1)[CH2:4][CH2:5][CH:6]([OH:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])#[N:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 178444110HCID 178444110, compound

Product 1

HCID 178444111HCID 178444111, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-cyano-1-(trans-4-methoxycyclohexyl)-4-decanone (48) (5.1 g, 17.4 mmol) obtained in the second step dissolved in 100 mL of THF and 50 mL of methanol was cooled with ice, to which sodium borohydride (0.79 g, 20.9 mmol) was then gradually added, followed by stirring under cooling with ice for 1 hour. The reaction mixture was put in 100 mL of iced water, and then extracted with 100 mL of ethyl acetate. The resulting organic layer was washed with water (100 mL×2) and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=4/1, column packing: silica gel) to obtain 1-cyano-1-(trans-4-methoxycyclohexyl)-4-decanol (49) (5.1 g, 17.4 mmol). The resulting compound was in the form of colorless crystals, and the yield based on the compound (48) was 100%.

Workup

  1. additionwas then gradually added
  2. temperatureunder cooling with ice for 1 hour
  3. extractionextracted with 100 mL of ethyl acetate
  4. washThe resulting organic layer was washed with water (100 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=4/1, column packing: silica gel)

Sources & evidence

ORD record
ord-e59e07f9e7eb49d99ce1c78ba2824f7f
Source dataset
uspto-grants-2011_01
Patent number
US07875327B2

Reaction notes

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