Tetrahydrofuran → HCID 10634688, compound

HRID 2212030Notes

Reaction equation

HRID 2212030 reaction equation
CC(C)([O-:4])C.[K+].[CH3:7][S:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(OCC)(=O)C>[CH2:20]([O:19][C:23](=[O:4])/[CH:22]=[CH:15]/[C:14]1[CH:17]=[CH:18][C:11]([S:8]([CH3:7])(=[O:10])=[O:9])=[CH:12][CH:13]=1)[CH3:21]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 2203764-(Methylsulfonyl)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 10634688HCID 10634688, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (10.96 g, 98 mmol) in tetrahydrofuran (60 ml) was added portionwise to a solution of triethyl phosphonoacetate (21.91 g, 98 mmol) in tetrahydrofuran (150 ml). The reaction mixture was stirred for 40 min at room temp. A solution of 4-(methylsulfonyl)benzaldehyde (Acros no.: 42490-0025; 10.0 g, 54 mmol) in tetrahydrofuran (60 ml) was added dropwise. The reaction mixture was stirred for 1 h at room temp. It was diluted with ethyl acetate (500 ml) and washed with 1 N hydrochloric acid (300 ml): The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by crystallization from ethyl acetate/heptane to give 4.3 g of (E)-3-(4-(methylsulfonyl)phenyl)acrylic acid ethyl ester.

Workup

  1. stirringThe reaction mixture was stirred for 1 h at room temp
  2. washwashed with 1 N hydrochloric acid (300 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by crystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-fbff0fa4d65d4ba1a0dd648e5bdd4cbe
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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