Acetic Acid → HCID 178520752, compound

HRID 1774389Notes

Reaction equation

HRID 1774389 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C.O>[CH2:12]([O:11][C:9]([CH2:8][C@H:5]1[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:12]([O:11][C:9]([CH2:8][C@@H:5]1[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 58069819Benzyl 2-(4-oxocyclohexyl)acetate

Product 2

HCID 178520751HCID 178520751, compoundYield 20%HCID 178520752HCID 178520752, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-(4-oxocyclohexyl)acetate (2.64 g, 10.7 mmol) in methanol (50 mL) was added sodium borohydride (393 mg, 10.4 mmol) with stirring under ice cooling. After stirring at the same temperature for 2 h, the reaction mixture was adjusted to pH 4 with acetic acid (1 mL). The reaction mixture was concentrated under reduced pressure, and the residue thus obtained was diluted with ethyl acetate and water to separate the layers. The aqueous layer was extracted again with ethyl acetate, and the combined organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate 3:1→2:1→1:1) to give 2.20 g of trans-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (yield: 82%) and 540 mg of cis-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (yield: 20%) as oil.

Workup

  1. stirringAfter stirring at the same temperature for 2 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue thus obtained
  4. customto separate the layers
  5. extractionThe aqueous layer was extracted again with ethyl acetate
  6. concentrationthe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e2790924e44041fbb7819c3c5ab3c694
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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