Bicarbonate Ion → rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate

HRID 2393901

反応式

HRID 2393901 の反応式
[O:1]1CCC[CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([O:13]C(=O)C)[CH:10]=[CH:9]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].C(=O)(O)[O-]>C(O)C.C(Cl)(Cl)Cl>[C:2]([O:7][C@@H:8]1[CH2:12][C@H:11]([OH:13])[CH:10]=[CH:9]1)(=[O:1])[CH3:3]

参加物

7

反応物 4

HCID 769Bicarbonate IonHCID 6101p-Toluenesulfonic acidHCID 19660Carbonate IonHCID 13623284(+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester

生成物 1

HCID 10154103rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate収率 75%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (192 mg, 0.85 mmol, prepared in example 11) in ethanol (1.5 mL) and treat with p-toluenesulfonic acid (11.7 mg). Stir the reaction at room temperature for 2 hours. Add carbonate or bicarbonate to neutralize the reaction mixture and concentrate under vacuum. Purify the residue by chromatography (silica gel, 3 g, 1.5×3 cm column, 33% ethyl acetate/hexane, 80 mL), to provide the title compound (90 mg, 75% yield, 91% ee), [α]20D =-66.1°, (c=0.63, chloroform).

後処理

  1. customthe reaction at room temperature for 2 hours
  2. concentrationconcentrate under vacuum
  3. customPurify the residue by chromatography (silica gel, 3 g, 1.5×3 cm column, 33% ethyl acetate/hexane, 80 mL)

出典と根拠

ORDレコード
ord-f14e0cc834e34b6ab34d7a780258cfdc
出典データセット
uspto-grants-1998_09
特許番号
US05808112

関連ノート

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