Potassium tert-butoxide → HCID 59289032, compound

HRID 386333Notes

Reaction equation

HRID 386333 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][CH:16]([CH:19]=O)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)[CH3:2].[CH3:22]C(C)([O-])C.[K+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][CH:16]([CH:19]=[CH2:22])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)[CH3:2]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59289027HCID 59289027, compound

Product 1

HCID 59289032HCID 59289032, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(4′-formyl-bicyclohexyl-4-yl)-propionic acid ethyl ester (7.8 g, 25 mmol) and methyltriphenylphosphoniumbromide (9.5 g, 26 mmol) in THF (150 ml) is added potassium-tert-butoxide portionwise at −10° C. The reaction mixture is stirred overnight, quenched with water and acidified with hydrochloric acid. The aq. layer is separated and extracted twice with MTB ether. The combined org. layers are washed with brine, dried (Na2SO4) and evaporated. The crude product is purified with heptane/ethyl acetate (19:1) on silica to give 3-(4′-vinyl-bicyclohexyl-4-yl)-propionic acid ethyl ester as a colourless solid.

Workup

  1. customquenched with water
  2. customThe aq. layer is separated
  3. extractionextracted twice with MTB ether
  4. washlayers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product is purified with heptane/ethyl acetate (19:1) on silica

Sources & evidence

ORD record
ord-fc91dbe505044f658d300c8f002c2745
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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