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Sodium borohydride → 1-Nitrohexane

HRID 979355
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HRID 979355 반응식
C(O[CH:5]([N+:11]([O-:13])=[O:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=O)C.C(O[CH:18]([CH2:34][CH2:35][C:36]([C:50]#[N:51])([CH:47]([CH3:49])[CH3:48])[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=1)[CH:19]([N+:31]([O-:33])=[O:32])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)(=O)C.[B].[BH4-].[Na+]>>[N+:11]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])([O-:13])=[O:12].[CH3:30][O:29][C:23]1[CH:22]=[C:21]([CH2:20][CH:19]([N+:31]([O-:33])=[O:32])[CH2:18][CH2:34][CH2:35][C:36]([C:50]#[N:51])([CH:47]([CH3:49])[CH3:48])[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 4311764Sodium borohydrideHCID 5462311BoronHCID 13745755O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-olHCID 88666005Nitrohexanol acetate

생성물 2

HCID 125891-NitrohexaneHCID 13745756
1-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane

실험 절차

The resulting nitrohexanol acetate of formula 9 is then reduced using a boron-based reducing agent, e.g., sodium borohydride, in a 2° or 3° alkanol at 25°-80° C. for 3-15 hours to produce a nitrohexane derivative of formula 10 (step 8). For example, O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol (9) is heated with NaBH4 in 2-propanol at reflux for 3-15 hours to yield 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane (10).

출처 및 근거

ORD 기록
ord-b7b53369e9204aa3b82b35534c61639f
출처 데이터셋
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04667038

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