HCID 19966471, compound → HCID 19966470, compound

HRID 1756341Notes

Reaction equation

HRID 1756341 reaction equation
[C:1]([O:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[CH:21]([O:30][C:31](=[O:33])[CH3:32])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][OH:10])(=[O:3])[CH3:2].CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[CH:21]([O:30][C:31](=[O:33])[CH3:32])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:12]=1)[CH2:6][CH2:7][CH2:8][CH:9]=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 19966471HCID 19966471, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19966470HCID 19966470, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 193 mg of the above-produced alcohol in 5 ml of methylene chloride is instilled in a mixture of 1.25 g of Collins reagent (chromic acid-pyridine complex) in 20 ml of methylene chloride at 0° C. with stirring, and it is stirred for 1 hour at 0° C. Then, enough Celite is added until a thick paste results, the latter is suspended with hexane/ethyl acetate (1:1), filtered off, washed well with hexane/ethyl acetate (1:1) and the filtrate is concentrated by evaporation in a vacuum. 150 mg of (5RS)-5-acetoxy-5-{3-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl)-pentanal is obtained as colorless oil.

Workup

  1. stirringit is stirred for 1 hour at 0° C
  2. additionThen, enough Celite is added until a thick paste
  3. customresults
  4. filtrationfiltered off
  5. washwashed well with hexane/ethyl acetate (1:1)
  6. concentrationthe filtrate is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-6712f487e3ab444db3a6dd5f3cabcc3b
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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