HCID 22184678, compound → HCID 22184671, compound

HRID 1795065Notes

Reaction equation

HRID 1795065 reaction equation
[CH:1]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:17]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:14]([CH3:16])[CH3:15])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1)([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 22184678HCID 22184678, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22184671HCID 22184671, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.5 g (54 mmol) of the alcohol from Step B in dichloromethane was added 20 g of Celite and 17.5 g (81 mmol) of pyridinium chlorochromate. The reaction mixture was stirred at room temperature for a 4 h period, and then filtered. The solids were washed with dichloromethane and the combined organic phases were concentrated. The residue was purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to give 13 g (85%) of the title compound. 1H NMR (500 MHz, CDCl3) δ 3.63 (d, 2H, J=4.9 Hz), 2.49–2.32 (m, 4H), 2.12 (m, 2H), 1.96 (m, 1H), 1.49 (m, 2H) 1.07 (d, 18H, J=5.5 hz), 1.06 (m, 3H).

Workup

  1. filtrationfiltered
  2. washThe solids were washed with dichloromethane
  3. concentrationthe combined organic phases were concentrated
  4. customThe residue was purified by flash chromatography on silica gel (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-20540a2b4397400e864cdc2e402451e0
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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