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

HRID 63324

반응식

HRID 63324 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-153e5b217a6840708a3c71eb2e2a633a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

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