Pyridine → HCID 86745529, compound

HRID 379638Notes

Reaction equation

HRID 379638 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1/[C:5](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)/[C:6]2[C:11]([C:12]=1[CH3:13])=[CH:10][CH:9]=[CH:8][CH:7]=2.N1C=CC=CC=1.CCOCC>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:5](=[CH:14]\[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)/[C:4]=1[CH2:3][CH:2]=[O:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 70231801HCID 70231801, compound

Product 1

HCID 86745529HCID 86745529, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the primary alcohol from Step 4 (1 g, 3.25 mmol) in dichloromethane (10 mL) was added dropwise to a mixture of chromium trioxide (3.3 g, 32 mmol, 10 eq.) in dichloromethane (50 mL) at 0° C. containing pyridine (5.1 mL, 63 mmol, 20 eq.). After 1.5 hour, ether was added to precipitate the chromium salts and the heterogenous mixture was filtered through silica gel and washed with ether. After evaporation to dryness, the residue was purified by chromatography on silica gel eluting with a 15:85 mixture of ethyl acetate-hexane to yield the title compound as a yellow oil.

Workup

  1. customto precipitate the chromium salts
  2. filtrationthe heterogenous mixture was filtered through silica gel
  3. washwashed with ether
  4. customAfter evaporation to dryness
  5. customthe residue was purified by chromatography on silica gel eluting with a 15:85 mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-56504e3a5b1f4f6a84598351a79a1c65
Source dataset
uspto-grants-2001_10
Patent number
US06300346B1

Reaction notes

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