Tetrahydrofuran → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

HRID 1484757ノート

反応式

HRID 1484757 の反応式
[Li].[CH3:2][C:3]([O-:6])(C)C.C[C:8]([O-:11])(C)C.CC([O-])(C)C.[Al+3].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>S(=O)(=O)(O)[O-].[Na+]>[OH:18][CH2:22][C:21]1([C:8]([O:6][CH2:3][CH3:2])=[O:11])[CH2:19][CH2:20]1

参加物

4

反応物 2

HCID 8028Tetrahydrofuran2 回HCID 6328594Aluminium lithium tri-tert-butoxide hydride

生成物 1

HCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate収率 91%

試薬・触媒・溶媒 1

HCID 516919Sodium Bisulfate溶媒

反応条件

温度
65 °C

実験手順

A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91%): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-2808f2b3e20444e1a3b7a7e8499cadcb
出典データセット
uspto-grants-2016_08
特許番号
US09422278B2

反応ノート

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