Oxygen → HCID 9910286, compound

HRID 324183Notes

Reaction equation

HRID 324183 reaction equation
[C:1]([C:5]1[C:6]([CH3:29])([CH3:28])[CH2:7][O:8][C:9]=1[C:10]1[CH:26]=[C:25]([OH:27])[C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[O:16][C:12]=2[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Na].[O:31]=[O:32]>C(Cl)Cl>[C:1]([C:5]12[O:32][O:31][C:9]1([C:10]1[CH:26]=[C:25]([OH:27])[C:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[O:16][C:12]=3[CH:11]=1)[O:8][CH2:7][C:6]2([CH3:29])[CH3:28])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 977OxygenHCID 5360545SodiumHCID 15547442HCID 15547442, compound2×

Product 1

HCID 9910286HCID 9910286, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5 mL of methylene chloride were added 1.0 mg of TPP and 95.1 mg (0.24 mmol) of 4-t-butyl-5-(4-hydroxy-2-(p-methoxyphenyl)benzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [67]), and the mixture was externally irradiated with a 940 W sodium lamp in an oxygen atmosphere for30 minutes. After the resulting mixture was concentrated, the concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=3:1), and then followed by recrystallization from the mixture of methylene chloride and hexane to obtain 95.8 mg of 5-t-butyl-1-(4-hydroxy-2-(p-methoxyphenyl)benzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (Compound [68]) as colorless granular micro-crystal. Yield 93.1%.

Workup

  1. concentrationAfter the resulting mixture was concentrated
  2. washthe elution
  3. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=3:1)
  4. customfollowed by recrystallization from the mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-47679892dffa4156b14a3a94557c866b
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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