Hydrochloric Acid → HCID 11094623, compound

HRID 615835Notes

Reaction equation

HRID 615835 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]=O)[CH2:3]1.Cl.[CH3:11]N(C)C=O>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C)C=CC=CC=1>[CH2:7]([CH:4]1[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]1)[CH:8]=[CH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 537697943-Hydroxy cyclopentyl-acetaldehyde

Product 1

HCID 11094623HCID 11094623, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
-60 °C

Procedure

A solution of 5 g of potassium tert.-butylate in 80 ml of dimethylformamide was added at -60° C. over 90 minutes to a solution of 5 g of 3-hydroxy-cyclopentyl-acetaldehyde, 15 g of triphenyl methyl phosphonium bromide and 100 ml of dimethylformamide and the resulting suspension was stirred at -60° C. for 2 hours after which the temperature was allowed to rise to 20° C. The mixture was poured into 2N hydrochloric acid solution and the mixture was extracted with isopropyl ether. The organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 cyclohexane-ethyl acetate mixture to obtain 1.7 g of 3-(2-propenyl)-cyclopentanol.

Workup

  1. customto rise to 20° C
  2. extractionthe mixture was extracted with isopropyl ether
  3. customThe organic phase was dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-97f749717d9a4559ba3d04068cf63b15
Source dataset
uspto-grants-1985_02
Patent number
US04501687

Reaction notes

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