Benzoic Acid → HCID 54154833、化合物

HRID 381688ノート

反応式

HRID 381688 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7](O)([CH3:9])C)=[CH:4][CH:3]=1.[C:11]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30]([OH:38])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:30]([O:38][C@@H:9]([CH2:7][C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 790016005-Chloro-α,α-dimethyl-2-thiophenemethanol

生成物 1

HCID 54154833HCID 54154833、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1(S)2-(5-chloro-2-thienyl-1-hydroxy-1-methylethane (5.7 g) in tetrahydrofuran (100 mL) is added triphenylphosphine (5.34 g) and benzoic acid (2.49 g). Diethyl azodicarboxylate (3.22 mL) is added dropwise and the mixture stirred at room temperature for about 18 hours. The solvent is removed in vacuo. The residue is purified by flash chromatography, eluting with 30% hexanes in methylene chloride, to give (R)-3-(5-chloro-2-thienyl)-2-propyl benzoate. The ester (3.91 g) is dissolved in dioxane (50 mL) and 20% aqueous sodium hydroxide (15 mL) is added. The mixture is heated at 55° C. for 3 hours and concentrated in vacuo. The residue is taken up in ethyl acetate (200 mL) and the organic layer washed with brine, dried over magnesium sulfate, filtered, concentrated in vacuo to give the desired product.

後処理

  1. customThe solvent is removed in vacuo
  2. customThe residue is purified by flash chromatography
  3. washeluting with 30% hexanes in methylene chloride

出典と根拠

ORDレコード
ord-22bc893539424840ae92c0c60430b588
出典データセット
uspto-grants-2001_10
特許番号
US06307054B1

反応ノート

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