Diethyl Ether → HCID 53653529, compound

HRID 638019Notes

Reaction equation

HRID 638019 reaction equation
[O:1]1[C@:5]([CH3:22])([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:21])[CH2:10][CH2:11][CH2:12][C@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:2]1[CH2:3][OH:4].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[O:1]1[C@:5]([CH3:22])([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:21])[CH2:10][CH2:11][CH2:12][C@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[C@@H:2]1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15917605HCID 15917605, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53653529HCID 53653529, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.70 g (5.45 mmol) of (2R,3R,7R,11R)-2,3-epoxy-3,7,11,15-tetramethylhexadecanol in 5 ml of methylene chloride was added dropwise while stirring at room temperature to a suspension of 1.6 g (5.45 mmol) of pyridinium chlorochromate in 50 ml of methylene chloride and the mixture was stirred at room temperature overnight. Celite was then added and the mixture was stirred with 100 ml of ether for 1 hour, subsequently filtered and rinsed with ether. The crude product was chromatographed on silica gel with toluene. There was obtained 1.46 g (87%) of (2R,3R,7R,11R)-2,3-epoxy-3,7,11,15-tetramethylhexadecanal, [α]D20 =-5.87° (c=1.5% in chloroform).

Workup

  1. additionCelite was then added
  2. filtrationsubsequently filtered
  3. washrinsed with ether
  4. customThe crude product was chromatographed on silica gel with toluene

Sources & evidence

ORD record
ord-c370193e86f14e1fb33ef3f5dbc5fa9d
Source dataset
uspto-grants-1985_12
Patent number
US04559407

Reaction notes

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