Tetrahydrofuran → HCID 86747310, compound

HRID 1654510Notes

Reaction equation

HRID 1654510 reaction equation
C([Li])C[CH2:3][CH3:4].[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([C:20]2(C=O)[CH2:25][CH2:24]OCC2)[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C[O:31][CH2:30][CH2:29]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:20]2[CH2:25][CH:24]([CH:3]=[CH2:4])[CH2:29][CH2:30][O:31]2)[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10447276HCID 10447276, compoundHCID 178418339Butyllithium

Product 1

HCID 86747310HCID 86747310, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl-lithium (1.6M in hexane, 1.375 ml) was added dropwise to a solution of methyltriphenylphosphonium bromide (0.786 g) in a mixture of THF (15 ml) and diethyl ether (2 ml). The mixture was stirred at ambient temperature for 2 hours. The solution so obtained was added dropwise to a solution of 4-(3-benzyloxyphenyl)-4-formyltetrahydropyran (0.592 g) in diethyl ether (10 ml) and the mixture was stirred at ambient temperature for 4 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p 40°-60° C.) and ethyl acetate as eluent. There was thus obtained 4-(3-benzyloxyphenyl-4-vinyltetrahydropyran (0.407 g, 70%), as an oil.

Workup

  1. customThe solution so obtained
  2. stirringthe mixture was stirred at ambient temperature for 4 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of petroleum ether (b.p 40°-60° C.) and ethyl acetate as eluent

Sources & evidence

ORD record
ord-cc195f5792104520a7a8e0f47d875eab
Source dataset
uspto-grants-1995_04
Patent number
US05407945

Reaction notes

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