Methane → HCID 6274528, compound

HRID 1034361Notes

Reaction equation

HRID 1034361 reaction equation
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:30]([C:38]([O:40][CH3:41])=[O:39])(=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.S([O-])([O-])(=O)=O.[Mg+2].C>CCOCC.O>[CH3:8][O:9]/[CH:10]=[C:30](\[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)/[C:38]([O:40][CH3:41])=[O:39]

Participants

8

Reactant 5

HCID 297MethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 84835Methyl phenylglyoxalateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 6274528HCID 6274528, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Potassium tert-butoxide (9.52 g) was added in a single portion to a stirred suspension of (methoxymethyl)-triphenylphosphonium chloride (34.3 g) in dry ether (300 ml). After 45 minutes, the resulting red suspension was treated with a solution of methyl benzoylformate (8.20 g) in dry ether (100 ml) (colour lightens; exotherm). After 3 hours, the mixture was diluted with water, treated with magnesium sulphate and charcoal, then concentrated under reduced pressure to give the crude produce (36.39 g) as a yellow oil which partially crystallised on standing. This was flushed through silica gel using dichloromethane, then carefully chromatographed using dichloromethane: petrol (2:1) to give E-methyl 3-methoxy-2-phenylpropenoate (4.83 g, 50% yield) as a pale yellow oil, eluted first, infrared (film): 1710, 1630 cm-1, 1H nmr (CDCl3): delta 7.55 (s, olefinic proton), and Z-methyl 3-methoxy-2-phenylpropenoate (3.43 g, 36% yield) as a pale yellow oil, eluted second, infrared (film): 1715, 1630 cm-1, 1H nmr (CDCl3): delta 3.76 (3H,s), 3.90 (3H,s), 6.65 (1H, s), 7.28 (5H,s) ppm.

Workup

  1. waitAfter 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customto give the crude
  4. customproduce (36.39 g) as a yellow oil which
  5. custompartially crystallised
  6. customThis was flushed through silica gel
  7. customcarefully chromatographed

Sources & evidence

ORD record
ord-f2865cea0f7f4a7b83522aa6b29b98a4
Source dataset
uspto-grants-1994_05
Patent number
US05315025

Reaction notes

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