Water → 4-(Hydroxymethyl)-3-methylbenzonitrile
반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=C)[C:5]#[N:6].[O:12]=[O+][O-].[BH4-].[Na+].O>CO>[OH:12][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]참가 물질
6
반응 조건
- 온도
- -70 °C
실험 절차
3-Methyl-4-vinylbenzonitrile (0.40 g; 2.8 mmol; from step (i) above) was dissolved in 50 mL of methanol and cooled to −70° C. Ozone (2 eq.) was bubbled through, and then 0.20 g (5.3 mmol) of sodium borohydride and 5 mL of water were added and the cooling bath was removed. After 4 h the methanol was evaporated and the residue was partitioned between 1M HCl and ether. The aqueous layer was extracted twice with ether and the combined organic phase was washed with water, dried (Na2SO4) and evaporated to yield 0.37 g (90%) of the desired product, which was used in the next step without further purification.
후처리
- additionwere added
- customthe cooling bath was removed
- customAfter 4 h the methanol was evaporated
- customthe residue was partitioned between 1M HCl and ether
- extractionThe aqueous layer was extracted twice with ether
- washthe combined organic phase was washed with water
- dry with materialdried (Na2SO4)
- customevaporated
출처 및 근거
- ORD 기록
- ord-6aa23f0416354da883ddf147d9477e39
- 출처 데이터셋
- uspto-grants-2002_01
- 특허 번호
- US06337394B2
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