Tetrahydrofuran → HCID 67226336, compound

HRID 2168437Notes

Reaction equation

HRID 2168437 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.O1CC[CH2:12][CH2:11]1>>[CH2:11]([C:6]1([OH:9])[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]1)[CH3:12]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 128928674-(Hydroxymethyl)cyclohexan-1-one

Product 1

HCID 67226336HCID 67226336, compound

Procedure

4-(Hydroxymethyl)cyclohexanone (1.22 g) in tetrahydrofuran (20 mL) was treated with 1-Methylmagnesium bromide in tetrahydrofuran (28.6 mL) at 0° C. The reaction was warmed to room temperature over 4 hours and quenched with methanol (2 mL) and water (2 mL). The resulting mixture was concentrated and the residue was suspended in ethyl acetate. The precipitates were filtered off and the filtrate was concentrated and purified by flash chromatography, eluted with 0-100% ethyl acetate in hexane to provide the title compound.

Workup

  1. customquenched with methanol (2 mL) and water (2 mL)
  2. concentrationThe resulting mixture was concentrated
  3. filtrationThe precipitates were filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified by flash chromatography
  6. washeluted with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b797087c81e1457ea508bfef84c9e4a2
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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