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

HRID 63324

反応式

HRID 63324 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-153e5b217a6840708a3c71eb2e2a633a
出典データセット
uspto-grants-2016_09
特許番号
US09447078B2

関連ノート

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