tert-Butanol → HCID 12952598, compound

HRID 1079004Notes

Reaction equation

HRID 1079004 reaction equation
[C:1](O)(C)(C)C.CC(C)([O-])C.[K+].[CH3:12][C:13]1[CH:17]([OH:18])[CH2:16][C:15](=O)[C:14]=1[CH2:20][CH:21]=[CH2:22].P([O-])(O)(O)=O.[Na+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH3:12][C:13]1[CH:17]([OH:18])[CH2:16][C:15](=[CH2:1])[C:14]=1[CH2:20][CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-HCID 23665647Potassium tert-butoxideHCID 23672064Monosodium phosphate

Product 1

HCID 12952598HCID 12952598, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Ether (125 ml), t-butanol (13.2 ml) and methyltriphenylphosphonium bromide (50 g) were mixed with stirring at room temperature, then potassium t-butoxide (25.7 g) was added portionwise to the mixture and then the resulting solution was stirred for 5 hours at the same temperature. To the solution was added a solution of (RS)-3-methyl-2-(2-propenyl)-4-hydroxy-cyclopent-2-ene-1-one (26.0 g) in ether (25 ml) under ice-water cooling and the resulting reaction mixture was stirred at the same temperature for 2 hours and then for 6 hours at room temperature. The reaction solution was poured into a saturated aqueous solution of sodium dihydrogenphosphate, and the product was extracted with ether. The obtained ether layer was washed with brine and dried over anhydrous magnesium sulfate. Then the filtered solution was evaporated. The obtained oily residue was then subjected to silica gel column chromatography to afford (RS)-2-methyl-4-methylidene3-(2-propenyl)cyclopent-2-ene-1-ol (10.0 g) in a yield of 40%.

Workup

  1. stirringthe resulting solution was stirred for 5 hours at the same temperature
  2. customthe resulting reaction mixture
  3. stirringwas stirred at the same temperature for 2 hours
  4. extractionthe product was extracted with ether
  5. washThe obtained ether layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen the filtered solution was evaporated

Sources & evidence

ORD record
ord-5c3ae12f60b74052abb2208dfb715c3d
Source dataset
uspto-grants-1996_08
Patent number
US05550260

Reaction notes

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