Sodium Acetate → HCID 86623587, compound

HRID 1986513Notes

Reaction equation

HRID 1986513 reaction equation
C([O-])(=O)C.[Na+].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:17][C:18]1([CH3:35])[CH2:23][CH2:22][C:21]([CH:24]([CH3:27])[CH2:25][OH:26])=[C:20]2[C:28]([CH3:34])([CH3:33])[CH:29]3[CH2:32][C:19]12[CH2:31][CH2:30]3>ClCCl>[CH3:35][C:18]1([CH3:17])[CH2:23][CH2:22][C:21]([CH:24]([CH3:27])[CH:25]=[O:26])=[C:20]2[C:28]([CH3:34])([CH3:33])[CH:29]3[CH2:32][C:19]12[CH2:31][CH2:30]3

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 688525241,3,4,5,6,7-Hexahydro-β,1,1,5,5-pentamethyl-2H-2,4a-methanonaphthalene-8-ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 86623587HCID 86623587, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium acetate (0.1 g) and PCC (6.6 g, 0.031 mol, portionwise) was added successively at r. t. to a vigorously stirred solution of 3b (6.0 g, 0.023 mol) in dichloromethane (200 ml). After additional 3 h stirring, the black reaction mixture was filtered through Celite®, the filtrate was concentrated in vacuo and purified by flash chromatography (MTBE/hexane 1:10) to give 2-(2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undec-5-en-5-yl)propanal (9b, 3.8 g, 64% yield, white solid).

Workup

  1. filtrationthe black reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash chromatography (MTBE/hexane 1:10)

Sources & evidence

ORD record
ord-070e5dc3a05e4aa98c3a3e7f7afddcce
Source dataset
uspto-grants-2009_06
Patent number
US07550417B2

Reaction notes

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