Oxygen → HCID 21940182, compound

HRID 352700Notes

Reaction equation

HRID 352700 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=2[C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Na].[O:37]=[O:38]>ClCCl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[O:38][O:37][C:12]2([C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:13]([CH3:17])([CH3:16])[CH2:14][O:15]3)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 977OxygenHCID 5360545SodiumHCID 21940188HCID 21940188, compound2×

Product 1

HCID 21940182HCID 21940182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(3-acetoxyphenyl)-4-(13-carboxy-1,1-dimethyl-3-oxatridecan-1-yl)-3,3-dimethyl-2,3-dihydrofuran (compound (22)) (125 mg, 0.256 mmol) and TPP (1 mg) were added to dichloromethane (12 mL), and the mixture was irradiated with visible light by a 940 W sodium lamp in an oxygen atmosphere at 0° C. for 30 minutes. The reaction mixture was concentrated, and the concentrate was put into a silica gel column and developed with a mixed solvent of hexane and ethyl acetate (10:1 to 5:1), whereby 1-(3-acetoxyphenyl)-5-(13-carboxy-1,1-dimethyl-3-oxatridecan-1-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (compound (23)) was obtained in an amount of 133 mg in a yield of 97.6%.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1f30e6edb524418a8819e6c8cf7ae5d5
Source dataset
uspto-grants-2004_06
Patent number
US06747160B2

Reaction notes

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