HCID 70653939, compound → HCID 67105609, compound

HRID 1042516Notes

Reaction equation

HRID 1042516 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:19]([C:21]1[C:22]([O:33][CH3:34])=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:21]1[C:22]([O:33][CH3:34])=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 70653939HCID 70653939, compound

Product 1

HCID 67105609HCID 67105609, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of crude 10 (4.5 mmol) in dichloromethane (80 mL) was treated with manganese dioxide (85%, 6 g, 15 equiv.) and this suspension was stirred at reflux for 6 hr. The solids were filtered out and washed with ethyl acetate. The solvent was removed in a rotary evaporator and the residue was chromatographed on silica (65 g) with 2% ethyl acetate in heptane (3 L). Pure 11 (1.2 g, 59%) was isolated.

Workup

  1. temperatureat reflux for 6 hr
  2. filtrationThe solids were filtered out
  3. washwashed with ethyl acetate
  4. customThe solvent was removed in a rotary evaporator
  5. customthe residue was chromatographed on silica (65 g) with 2% ethyl acetate in heptane (3 L)

Sources & evidence

ORD record
ord-a7e7cde2acdb4b25923376639393f9a8
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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