HCID 178471800, compound → HCID 178471796, compound

HRID 505274Notes

Reaction equation

HRID 505274 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12](O)=[O:13])[CH2:8][CH2:7]1)[CH3:2]>C1COCC1>[OH:13][CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH2:7][CH2:8]1

Participants

3

Reactant 1

HCID 178471800HCID 178471800, compound

Product 1

HCID 178471796HCID 178471796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trans-4-(2-ethoxy-2-oxoethyl)cyclohexanecarboxylic acid (385.6 mg, 1.80 mmol) in THF (20 mL) was added BH3 (2.7 mL of a 1M solution in THF, 2.70 mmol). After 2 hours, the reaction was quenched by careful addition of H2O (10 mL). The mixture was extracted with EtOAc (80 mL) and the organic layer was washed with water and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 60% EtOAc/hexanes) afforded ethyl [trans-4-(hydroxymethyl)cyclohexyl]acetate. Rf=0.26 (40% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 4.12 (q, J=7.1 Hz, 2H), 3.45 (d, J=6.5 Hz, 2H), 2.19 (d, J=7.0 Hz, 2H), 1.72-1.82 (m, 5H), 1.45 (m, 1H), 1.25 (t, J=7.1 Hz, 3H), 0.96-1.05 (m, 4H).

Workup

  1. customthe reaction was quenched by careful addition of H2O (10 mL)
  2. extractionThe mixture was extracted with EtOAc (80 mL)
  3. washthe organic layer was washed with water and brine (20 mL each)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (5 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-623152c8758a445f868eca0648c78895
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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