Monobenzone → Benzene, (hexyloxy)-

HRID 980498노트

반응식

HRID 980498 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=1)[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

4

반응물 2

HCID 7638MonobenzoneHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 517985Benzene, (hexyloxy)-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a three-neck flask flushed with argon and fitted with a magnetic stir bar was added 30 ml of dry THF, 1.379 gm (6.9 mmol) of p-benzyloxyphenol (the compound of Formula IV), 0.8 gm (6.9 mmol) of (2S,3S)-3-prophloxiranemethanol (the compound of Formula V), and 1.98 gm (7.59 mmol) of triphenylphosophine. The resulting solution was heated to reflux and 1.2 ml (1.32 gm, 7.59 mmol) of diethyl azodicarboxylate was added over a period of 7 hr. After the addition was complete the reaction mixture was allowed to cool to room temperature and stir for an additional two days under argon. The solvent was then removed, and the residue purified by flash chromatography on silica gel using 85:15 hexanes/ethyl acetate as eluent. In this manner 1.6 gm (78%) of 4-benzyloxy-1-[2S,3S)-epoxy]-hexyloxybenzene (the compound of Formula VI) was obtained.

후처리

  1. customTo a three-neck flask flushed with argon
  2. customfitted with a magnetic stir bar
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux
  5. additionAfter the addition
  6. customThe solvent was then removed
  7. customthe residue purified by flash chromatography on silica gel using 85:15 hexanes/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-a86d9becd4224dad985afcbba29871e4
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04638073

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