Water → HCID 67884025, compound

HRID 256551Notes

Reaction equation

HRID 256551 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[CH2:26]([C:33]1[CH:37]=[CH:36][S:35][C:34]=1[C:38](=O)[C:39]([O:41][CH3:42])=[O:40])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C1COCC1>[CH2:26]([C:33]1[CH:37]=[CH:36][S:35][C:34]=1/[C:38](=[CH:2]\[O:3][CH3:4])/[C:39]([O:41][CH3:42])=[O:40])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amide2×HCID 2723798Methoxymethyl-triphenylphosphonium chloride2×HCID 19785054HCID 19785054, compound

Product 1

HCID 67884025HCID 67884025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of (methoxymethyl)triphenylphosphonium chloride and sodamide (0.4 g of a 1:1 molar mixture) in dry THF was added a solution of methyl 2-(3-benzyl-2-thienyl)-2-oxoacetate (220 mg, 0.8 mmol) in dry THF (5 ml). The reaction mixture was stirred at room temperature for 30 minutes. More (methoxymethyl)triphenylphosphonium chloride and sodamide (0.2 g of a 1:1 molar mixture) were added and stirring was continued for a further one hour. The reaction mixture was poured into water and then extracted with ether. The combined ether layers were washed with water and brine and then dried. Filtration through a pad of silica gel to remove triphenylphosphine oxide, followed by HPLC (eluent dichloromethane) afforded (Z)-methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate, an oil (100 mg), 1H nmr: delta 3.64 (3H, s), 3.78 (6H,s), 6.75 (1H,d), 7.0-7.4 (6H,m), 7.60 (1H,s) ppm; and (E)-methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate, an oil (30 mg), 1H nmr: delta 3.64 (3H,s), 3.80 (3H,s), 3.82 (3H,s), 6.56 (1H,s), 6.75 (1H,d), 7.0-7.3 (6H,m) ppm.

Workup

  1. stirringstirring
  2. waitwas continued for a further one hour
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with water and brine
  5. customdried
  6. filtrationFiltration through a pad of silica gel
  7. customto remove triphenylphosphine oxide

Sources & evidence

ORD record
ord-54522b9355424640848588b384001c60
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Reaction notes

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