Diethyl Ether → HCID 9881685, compound

HRID 1019243Notes

Reaction equation

HRID 1019243 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:12][C@:13]12[CH2:23][CH2:22][C@@H:21]3[CH2:24][C@:18]1([O:19][C:20]3([CH3:26])[CH3:25])[C:17]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:16][CH2:15][CH2:14]2.CCOCC>C(Cl)Cl>[CH3:12][C@:13]12[CH2:23][CH2:22][C@@H:21]3[CH2:24][C@:18]1([O:19][C:20]3([CH3:25])[CH3:26])[C:17]([CH2:27][CH2:28][CH:29]=[O:30])=[CH:16][CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15512998HCID 15512998, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 9881685HCID 9881685, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

300 mg (1.39 mmol) of PCC was added to a solution of 100 mg (0.38 mmol) of (1R,6S,9R)6,10,10-trimethyl-2-(3-hydroxypropyl)-11-oxatricyclo[7.2.1.01,6]dodec-2-ene from example 12 in 15 ml of methylene chloride and the reaction mixture was stirred at room temperature for 3 hours, then was added 15 mL of ether. After filtration, the filtrate was concentrated to give 90 mg of crude product.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f2c040f3902049b7816ae52ace7b785a
Source dataset
uspto-grants-2002_11
Patent number
US06486201B1

Reaction notes

Loading…