Methoxymethyl-triphenylphosphonium chloride → HCID 73996565, compound

HRID 1007054Notes

Reaction equation

HRID 1007054 reaction equation
C1([Li])C=CC=CC=1.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:31][C:32]1[C:37]([F:38])=[C:36]([F:39])[CH:35]=[C:34]([C:40]2[CH:45]=[CH:44][C:43]([CH:46]3[CH2:51][CH2:50][CH:49]([CH2:52][CH2:53][CH3:54])[CH2:48][CH2:47]3)=[CH:42][CH:41]=2)[C:33]=1C=O.C1CCCCC1.[CH2:63]([O:65][CH2:66][CH3:67])C>C(OCC)C>[F:31][C:32]1[C:33]([CH:67]=[CH:66][O:65][CH3:63])=[C:34]([C:40]2[CH:45]=[CH:44][C:43]([CH:46]3[CH2:51][CH2:50][CH:49]([CH2:52][CH2:53][CH3:54])[CH2:48][CH2:47]3)=[CH:42][CH:41]=2)[CH:35]=[C:36]([F:39])[C:37]=1[F:38]

Participants

6

Reactant 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 21895417Cyclohexane diethyletherHCID 22667439HCID 22667439, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 73996565HCID 73996565, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-50 °C

Procedure

27 ml (48 mmol) of a 1.8 M solution of phenyllithium in cyclohexane/diethyl ether (7:3) are added dropwise at −65° C. to a solution/suspension of 45 mmol of methoxymethyltriphenylphosphonium chloride in 280 ml of dry diethyl ether. The mixture is stirred at the same temperature for 30 minutes, then kept at −10° C. for 30 minutes and subsequently re-cooled to −50° C. 16 mmol of 3,4,5-trifluoro-4′-(4-propylcyclohexyl)biphenyl -2-carbaldehyde are added at this temperature. The reaction mixture is allowed to thaw slowly, and stirring is continued at room temperature. Ice-water is added to the reaction mixture, and the organic phase is separated off and washed with cold water. After drying using sodium sulfate, the mixture is evaporated under reduced pressure, and the residue is stirred with n-heptane and filtered. The filtrate is chromatographed on silica gel (n-heptane/ethyl acetate 98:2), giving 3,4,5-trifluoro-2-(2-methoxyvinyl)-4′-(4-propylcyclohexyl)biphenyl (mixture of Z and E isomers).

Workup

  1. waitkept at −10° C. for 30 minutes
  2. stirringstirring
  3. customis continued at room temperature
  4. customthe organic phase is separated off
  5. washwashed with cold water
  6. customAfter drying
  7. customthe mixture is evaporated under reduced pressure
  8. stirringthe residue is stirred with n-heptane
  9. filtrationfiltered
  10. customThe filtrate is chromatographed on silica gel (n-heptane/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-29f99b8dd5824dc9bfa914fae2af9e47
Source dataset
uspto-grants-2004_09
Patent number
US06793984B2

Reaction notes

Loading…