Oxygen → 5-t-Butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

HRID 324179Notes

Reaction equation

HRID 324179 reaction equation
[C:1]([C:5]1[C:6]([CH3:27])([CH3:26])[CH2:7][O:8][C:9]=1[C:10]1[CH:24]=[C:23]([OH:25])[C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:16][C:12]=2[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Na].[O:29]=[O:30]>C(Cl)Cl>[C:1]([C:5]12[O:30][O:29][C:9]1([C:10]1[CH:24]=[C:23]([OH:25])[C:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:16][C:12]=3[CH:11]=1)[O:8][CH2:7][C:6]2([CH3:27])[CH3:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 977OxygenHCID 5360545SodiumHCID 155474404-t-Butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran2×

Product 1

HCID 98008245-t-Butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptaneYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 15 mL of methylene chloride were added 1.0 mg of TPP and 156 mg (0.43 mmol) of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63]), and the mixture was externally irradiated with a 940 W sodium lamp in an oxygen atmosphere for 30 minutes, then 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:ether =1:1) to obtain 25.3 mg of 5-t-butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (Compound [64]) as colorless granular crystal. Yield 85.1%.

Workup

  1. concentrationconcentrated
  2. washthe elution
  3. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ether =1:1)

Sources & evidence

ORD record
ord-c6a65e81e5fe44029ea42f7b304f4597
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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