Acetaldehyde → Methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate

HRID 873723ノート

反応式

HRID 873723 の反応式
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][O:14][C:15]1([O:23][CH3:24])[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]1.[CH:25](=[O:27])[CH3:26]>C1COCC1.O>[OH:27][CH:25]([C:17]1([C:19]([O:21][CH3:22])=[O:20])[CH2:16][C:15]([O:14][CH3:13])([O:23][CH3:24])[CH2:18]1)[CH3:26]

参加物

7

反応物 4

HCID 177AcetaldehydeHCID 7912DiisopropylamineHCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 86724266Methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate収率 88.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a solution of diisopropylamine (3.2 mL, 22.67 mmol) in THF (45 mL) was added n-BuLi (2.69 M in hexane, 7.7 mL, 20.71 mmol) at −78° C. under argon. The mixture was stirred for 10 minutes at 0° C., then cooled to −78° C. and added a solution of methyl 3,3-dimethoxycyclobutanecarboxylate (3.0 g, 17.22 mmol) in THF (10 mL). The mixture was stirred for 30 minutes at −78° C., then added a solution of acetaldehyde (1.9 mL, 33.86 mmol) in THF (10 mL). The mixture was stirred for 30 minutes at −78° C., and water was added. The aqueous layer was extracted with EtOAc. Combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure to give methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate (3.33 g).

後処理

  1. temperaturecooled to −78° C.
  2. stirringThe mixture was stirred for 30 minutes at −78° C.
  3. stirringThe mixture was stirred for 30 minutes at −78° C.
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-6bbb94ad91dc4247a6febf44a6d922aa
出典データセット
uspto-grants-2015_03
特許番号
US08975415B2

反応ノート

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