HCID 25030274, compound → HCID 25029795, compound

HRID 2280584Notes

Reaction equation

HRID 2280584 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1

Participants

6

Reactant 2

HCID 25030274HCID 25030274, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 25029795HCID 25029795, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Alcohol 9 was dissolved in 8 mls of DCM, followed by the addition of PCC (4 eq, 2.63 mM) and celite the reaction mixture was stirred for 8 hours, after which it was diluted with ether, followed by washes with bicarb solution and brine. The organic layer was separated and dried under reduced pressure. The product was the subjected to flash chromatography using 20% EtOAc/hexanes as the solvent system to obtain the product as a white solid. Yield=90.5% (Rf=0.57; 20% EtOAc/Hexanes), 1H NMR, 500 MHz Varian, CDCl3, δ 7.86 (d, J=10.00 Hz, 1H), 7.84 (d, J=15.00 Hz, 1H), 7.58 (m, 1H), 7.52 (s, 1H), 7.50 (s, 1H), 7.48 (s, 1H), 7.38 (d, J=10.00, 1H), 7.36 (d, J=9.5 Hz, 2H), 7.33 (t, J=15.5 Hz, 1H), 7.19 (d, J=7.5, 1H), 3.86\ (s, 3H), 2.41 (s, 3H) MS: m/z (ESI, pos.)=325.3 ([M+23])

Workup

  1. customThe organic layer was separated
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-ae9ac3b8238f41c5905ab99232af0476
Source dataset
uspto-grants-2015_09
Patent number
US09139546B2

Reaction notes

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