HCID 14022229, compound → HCID 13715839, compound

HRID 9807Notes

Reaction equation

HRID 9807 reaction equation
[C:1]1(=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 14022229HCID 14022229, compound

Product 1

HCID 13715839HCID 13715839, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-cyclopentylidene-hexan-1-ol (1.15 g, 6.85 mmol) in MeOH (50 mL) was hydrogenated with Pd—C (0.25 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclopentyl-hexan-1-ol (1.30 g, 100%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.63 (2H, t, J=6.6 Hz), 1.42–1.64 (6H, m), 1.20–1.40 (8H, m), 1.04(2H, m); 13C NMR (75 MHz, CDCl3) δ 63.28, 40.41, 36.43, 33.06, 33.00, 29.98, 29.04, 26.05, 25.47.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7527adbc893f41bcbd88fd23ee6e45f9
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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