Ethyl Acetate → cis 3a,4,5,7a-tetrahydro-2(3H)-benzofuranone

HRID 846530

反応式

HRID 846530 の反応式
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[C:14]([CH2:19][CH:20]1[C:25](=[O:26])[CH:24]=[CH:23][CH2:22][CH2:21]1)([O:16]CC)=O.C(C(C(C([O-])=O)O)O)(O)=O.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:26]1[C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][C@H:20]2[CH2:19][C:14]1=[O:16]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11143Aluminum isopropoxideHCID 13834278Ethyl (2-oxo-cyclohex-3-enyl)acetateHCID 23690454Sodium 3-carboxy-2,3-dihydroxypropanoate

生成物 1

HCID 11205783cis 3a,4,5,7a-tetrahydro-2(3H)-benzofuranone収率 86%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a solution of 13.5 g (66.0 mmoles) of aluminum isopropoxide in 100 ml of toluene was added 2.0 g (11.0 mmoles) of 6-(carbethoxymethyl)-2-cyclohexen-1-one at room temperature, and the solution was heated to 90° C. for 18 hours. The solution was cooled to room temperature, and aqueous saturated sodium hydrogen tartrate and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate, and the combined ethyl acetate extracts were dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The crude material was purified by Kugelrohr distillation (bp 40°-80° C./0.01 mm Hg) to yield 1.3 g (86%) of cis 3a,4,5,7a-tetrahydro-2(3H)-benzofuranone, as confirmed by NMR and IR data.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. distillationThe crude material was purified by Kugelrohr distillation (bp 40°-80° C./0.01 mm Hg)

出典と根拠

ORDレコード
ord-b2d6c0049ace41d3a351d491dc0f1323
出典データセット
uspto-grants-1992_08
特許番号
US05137035

関連ノート

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