Sodium Carbonate → HCID 86684841, compound

HRID 537834Notes

Reaction equation

HRID 537834 reaction equation
[Si:1]([O:18][C@H:19]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Si:1]([O:18][C@H:19]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 57500216HCID 57500216, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86684841HCID 86684841, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R,Z)-12-(tert-butyldiphenylsilyloxy)octadec-9-en-1-ol (11.1 g, 21.2 mmol) in anhydrous dichloromethane (160 mL) was added pyridinium chlorochromate (215.6 g, 110.3 mmol) and sodium carbonate (1.1 g, 18.4 mmol). The mixture was stirred at room temperature for 3 hours then filtered through a pad of silica (eluted with 100% ethyl acetate). The filtrate was concentrated in vacuo to dryness and the residue was purified by column chromatography (gradient: 100% hexanes to 10% ethyl acetate in hexanes) to afford the title compound as a yellow oil (8.9 g, 81%).

Workup

  1. filtrationthen filtered through a pad of silica (eluted with 100% ethyl acetate)
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. customthe residue was purified by column chromatography (gradient: 100% hexanes to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c6d3da098d354eb5b875d24706b478cc
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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