Benzoic Acid → HCID 54154833, 화합물

HRID 381688노트

반응식

HRID 381688 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 54154833HCID 54154833, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-22bc893539424840ae92c0c60430b588
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307054B1

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