Water → Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate

HRID 344614

Reaction equation

HRID 344614 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl-].COC[P+]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(C1C=CC=CC=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O([CH2:37][C:38]1[CH:42]=[CH:41][S:40][C:39]=1[C:43](=[O:48])[C:44]([O:46][CH3:47])=[O:45])C1C=CC=CC=1.[OH2:49].[CH2:50]1[CH2:54][O:53][CH2:52][CH2:51]1>CCOCC>[C:43]([C:39]1[S:40][CH:41]=[C:42](/[C:50](=[CH:51]\[O:4][CH3:2])/[C:54]([O:53][CH3:52])=[O:49])[CH:38]=1)(=[O:48])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH2:37]([C:38]1[CH:42]=[CH:41][S:40][C:39]=1[C:43](=[CH:52][O:53][CH3:54])[C:44]([O:46][CH3:47])=[O:45])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 14326170HCID 14326170, compoundHCID 23665647Potassium tert-butoxide

Product 2

HCID 54504656Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoateHCID 67883648HCID 67883648, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium tert-butoxide (844 mg) was added in one portion to a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (2.86 g) in ether (30 ml). The reaction mixture became red. After 20 minutes, a solution of methyl 2-(3-phenoxymethyl-2-thienyl)-2-oxoacetate (770 mg) in THF (10 ml) was added in one portion and the red colour was discharged. The resulting mixture was stirred at room temperature for 30 minutes then poured into water. The organic and aqueous layers were separated, and the latter was extracted with ether. The combined organic layers were washed with water, dried, concentrated and chromatographed using a 1:1 mixture of ether and petrol as eluent to give (i) the (Z)-isomer of the title compound (230 mg, 27%) as a pale yellow oil, IR (film) 1710, 1625 cm-1, 1H nmr: see Table VII; and (ii) the (E)-isomer of the title compound (80 mg, 9% yield), also a pale yellow oil, IR (film) 1700, 1620 cm-1, 1H nmr: see Table VII.

Workup

  1. customThe organic and aqueous layers were separated
  2. extractionthe latter was extracted with ether
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed
  7. additiona 1:1 mixture of ether and petrol as eluent

Sources & evidence

ORD record
ord-2b6c81f1c1cb49139f05897cf5d6b050
Source dataset
uspto-grants-1991_10
Patent number
US05053073

Linked notes

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