Triphenylphosphine → HCID 22042256, compound

HRID 1791045Notes

Reaction equation

HRID 1791045 reaction equation
I[CH2:2][C:3](=[CH2:18])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH:16]=O.ClCC(=C)COC1C=CC(C(OC)=O)=CC=1C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[O-].[Na+]>CO.C(#N)C>[CH2:2]=[C:3]1[CH:18]=[CH:16][C:7]2[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 10942334Sodium MethoxideHCID 22042282Methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoateHCID 22042284Methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate

Product 1

HCID 22042256HCID 22042256, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

333 mg (1 mmol) of a 60/40 mixture of methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoate and of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate and then 297 mg (1.133 mmol) of triphenylphosphine are successively introduced into the 50 ml single-necked flask. The combined mixture is subjected to a stream of nitrogen and then 20 ml of acetonitrile are introduced via a hollow tube. After complete dissolution, the solution is brought to reflux overnight. After cooling the solution, 0.23 ml (1 mmol) of a solution of sodium methoxide in methanol is added dropwise and the medium is stirred for a further one hour. After the usual treatments, 120 mg (54%) of methyl 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylate are obtained in the form of a white solid; 1H NMR (300 MHz, CDCl3): 7.95 (d, J=1.8 Hz, 1H), 7.82 (dd, J=1.8 Hz and 8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 6.51 (d, J=12 Hz, 1H), 6.38 (d, J=12 Hz, 1H), 5.28 and 5.11 (2s, 2H), 4.61 (s, 2H), 3.89 (s, 3H).

Workup

  1. dissolutionAfter complete dissolution
  2. temperatureto reflux overnight
  3. additionis added dropwise

Sources & evidence

ORD record
ord-f5df823ed3eb434a8e25c7760acc0ac2
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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