Monobenzone → Benzene, (hexyloxy)-

HRID 980498ノート

反応式

HRID 980498 の反応式
[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]

参加物

4

反応物 2

HCID 7638MonobenzoneHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 517985Benzene, (hexyloxy)-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a86d9becd4224dad985afcbba29871e4
出典データセット
uspto-grants-1987_01
特許番号
US04638073

反応ノート

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