Benzoic Acid → HCID 54154833, compound

HRID 381688Notes

Reaction equation

HRID 381688 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 54154833HCID 54154833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-22bc893539424840ae92c0c60430b588
Source dataset
uspto-grants-2001_10
Patent number
US06307054B1

Reaction notes

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