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

HRID 324181Notes

Reaction equation

HRID 324181 reaction equation
[C:1]([C:5]1[C:6]([CH3:34])([CH3:33])[CH2:7][O:8][C:9]=1[C:10]1[CH:24]=[C:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[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].C(Cl)Cl.[Na].[O:39]=[O:40]>>[C:1]([C:5]12[O:40][O:39][C:9]1([C:10]1[CH:24]=[C:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[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([CH3:34])[CH3:33])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 977OxygenHCID 6344DichloromethaneHCID 5360545SodiumHCID 155474414-t-Butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran2×

Product 1

HCID 99142795-t-Butyl-1-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptaneYield 85.1%

Procedure

Adding 1 mg of TPP and 27.9 mg (0.058 mmol) of 4-t-butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran (Compound [65]) to 5 ml of methylene chloride, the mixture was externally irritated with a 940 W sodium lamp for 30 minutes in oxygen atmosphere. After concentrated, the resulting mixture was applied to a silica gel column and the elution was carried out the mixture of hexane and ethyl acetate (hexane:ethyl acetate=15:1) to obtain 25.3 mg of 5-t-butyl-1-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (Compound [66]) as a purple oil. Yield 85.1%.

Workup

  1. concentrationAfter concentrated
  2. washthe elution
  3. additionthe mixture of hexane and ethyl acetate (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-0f87a46c7a5c47a1b37125a3f8344579
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

Loading…