(Chloromethyl)triphenylphosphonium chloride → HCID 69666534, compound

HRID 1791038Notes

Reaction equation

HRID 1791038 reaction equation
C([Li])CCC.[Cl-].[Cl:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:28]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]=[CH:31][C:30](=O)[CH2:29]1>O1CCCC1.CCCCC>[Cl:7][CH:8]=[C:30]1[CH:31]=[CH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:28][CH2:29]1

Participants

6

Reactant 3

HCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 112636571-Benzoxepin-3(2H)-oneHCID 178418339Butyllithium

Product 1

HCID 69666534HCID 69666534, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.1 eq. of n-butyllithium are added to 104 mg (0.3 mmol) of chloromethyltriphenylphosphonium chloride in solution in tetrahydrofuran cooled to 0° C. After stirring for one hour, 40 mg (0.25 mmol) of 1-benzoxepin-3(2H)-one, prepared according to example 25, are added at ambient temperature and the mixture is left for 1 hour. After the usual treatments and evaporating the solvent under reduced pressure, the crude reaction product is taken up in pentane in order to precipitate triphenylphosphine oxide, to give 25 mg (52%) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin in the form of two isomers as a Z/E mixture (90/10); 1H NMR (300 MHz, C6D6) 6.98–6.78 (m, 4H), 6.02 (d, J=11.8 Hz, 1H), 5.80 (d, J=11.8 Hz, 1H), 5.68 (s, 1H), 4.65 (4.06) (s, 2H).

Workup

  1. additionare added at ambient temperature
  2. waitthe mixture is left for 1 hour
  3. customAfter the usual treatments and evaporating the solvent under reduced pressure
  4. customthe crude reaction product
  5. customto precipitate triphenylphosphine oxide

Sources & evidence

ORD record
ord-acfe2cd6cd61488092e8115fdd52e651
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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