Water → Methyl 6-(4-methoxycarbonylbenzyl)-8-(2-methoxyphenyl)-7-octenoate

HRID 2243299Notes

Reaction equation

HRID 2243299 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([CH:32]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([O:50][CH3:51])=[O:49])=[CH:44][CH:43]=1)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=O.O>C1COCC1>[CH3:51][O:50][C:48]([C:45]1[CH:46]=[CH:47][C:42]([CH2:41][CH:32]([CH:30]=[CH:6][C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[O:3][CH3:2])[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:43][CH:44]=1)=[O:49]

Participants

5

Reactant 3

HCID 962WaterHCID 11255212Methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoateHCID 11294197Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromide

Product 1

HCID 68707125Methyl 6-(4-methoxycarbonylbenzyl)-8-(2-methoxyphenyl)-7-octenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., 77.4 mg (0.17 mmol) of 2-methoxybenzyltriphenylphosphonium bromide from Ex. IVj are suspended under argon in 20 ml of THF, and 0.115 ml of buthyl-lithium (0.18 mmol, 1.6 M solution in hexane) are added. The deep-orange solution is stirred at 0° C. for 30 min. At this temperature, a solution of 51.2 mg (0.17 mmol) of methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoate (synthesis analogously to EP-A-0 341 551, p. 32, Ex. 44) in 15 ml of THF is added dropwise. The mixture is stirred at 0° C. for 30 min. At 0° C., water is added and the mixture is warmed to room temperature and extracted with ethyl acetate. The organic phase is washed with sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. For purification, the substance is chromatographed on silica gel 60 (particle size 0.040-0.063 mm) using cyclohexane/ethyl acetate 9:1 to 1:1 as mobile phase.

Workup

  1. customAt 0° C.
  2. stirringThe mixture is stirred at 0° C. for 30 min
  3. temperaturethe mixture is warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customFor purification
  9. customthe substance is chromatographed on silica gel 60 (particle size 0.040-0.063 mm)

Sources & evidence

ORD record
ord-55972a5603f14e849eee434b786a63f3
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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