Oxygen → HCID 15545872, compound

HRID 324171Notes

Reaction equation

HRID 324171 reaction equation
C(Cl)Cl.[C:4]([C:8]1[C:9]([CH3:31])([CH3:30])[CH2:10][O:11][C:12]=1[C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:18][C:16]=2[CH:17]=1)([CH3:7])([CH3:6])[CH3:5].[Na].[O:33]=[O:34]>>[C:4]([C:8]12[O:34][O:33][C:12]1([C:13]1[O:14][C:15]3[CH:21]=[CH:20][C:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])=[CH:18][C:16]=3[CH:17]=1)[O:11][CH2:10][C:9]2([CH3:31])[CH3:30])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 4

HCID 977OxygenHCID 6344DichloromethaneHCID 5360545SodiumHCID 15547434HCID 15547434, compound2×

Product 1

HCID 15545872HCID 15545872, compoundYield 85%

Procedure

Adding 1 mg of TPP to 4 ml of methylene chloride dissolving 132 mg (0.286 mmol) of 4-t-butyl-5-(5-(t-butyldimethylsiloxy)benzofuran-2-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [18]), the mixture was stirred in oxygen atmosphere, at the temperature of −78° C. This solution was externally irritated with a 940 W sodium lamp for 4 hours. The reaction mixture was concentrated and fractionated with aliquot thin layer chromatography using the mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:1) to obtain 114 mg of 5-t-butyl-1-(5-(t-butyldimethylsiloxy)benzofuran-2-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (Compound [19]) as a white solid. Yield 85.0%.

Workup

  1. customat the temperature of −78° C
  2. concentrationThe reaction mixture was concentrated
  3. additionthe mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-a5ee80bd11ff4f59994248e1745b042e
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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