Cyclohexanemethanol → Cyclohexylmethyl 5-(cyclohexylmethoxy)furan-2-carboxylate

HRID 63324

Reaction equation

HRID 63324 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:12]1[O:16][C:15]([C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:18])=[CH:14][CH:13]=1>CN1C(=O)CCC1>[CH:1]1([CH2:7][O:8][C:12]2[O:16][C:15]([C:17]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7507CyclohexanemethanolHCID 24758Sodium hydrideHCID 86694615Cyclohexylmethyl 5-bromofuran-2-carboxylate

Product 1

HCID 86694619Cyclohexylmethyl 5-(cyclohexylmethoxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Cyclohexylmethanol (1.60 g, 14.0 mmol) was slowly added to a cooled (0° C.) suspension of sodium hydride (0.30 g, 12.5 mmol) in anhydrous NMP (5 mL) under Ar. A solution of cyclohexylmethyl 5-bromofuran-2-carboxylate (1.79 g, 6.23 mmol) in anhydrous NMP (6 mL) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was partitioned between aqueous NH4Cl (25%) and hexanes. Aqueous layer was extracted with hexanes and combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (2%-10% EtOAc—hexanes gradient) gave cyclohexylmethyl 5-(cyclohexylmethoxy)furan-2-carboxylate as a colorless oil. Yield (1.05 g, 53%); 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=3.4 Hz, 1H), 5.27 (d, J=3.9 Hz, 1H), 4.05 (d, J=6.4 Hz, 2H), 3.91 (d, J=5.9 Hz, 2H), 1.62-1.85 (m, 12H), 1.10-1.33 (m, 6H), 0.94-1.10 (m, 4H).

Workup

  1. temperaturea cooled
  2. customThe reaction mixture was partitioned between aqueous NH4Cl (25%) and hexanes
  3. extractionAqueous layer was extracted with hexanes
  4. washwere washed with brine
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (2%-10% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-153e5b217a6840708a3c71eb2e2a633a
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Linked notes

Loading…