Toluene → HCID 10064622, 화합물

HRID 1029544노트

반응식

HRID 1029544 반응식
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]([NH:23][NH2:24])=[O:22])([CH3:15])[CH3:14]>O1CCCC1.C(OCC)(=O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]1[O:22][C:1](=[O:2])[NH:24][N:23]=1)([CH3:12])[CH3:14]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 6371PhosgeneHCID 10424537HCID 10424537, 화합물

생성물 1

HCID 10064622HCID 10064622, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A 12.5% solution of phosgene in toluene (2.4 mL, 2.7 mmol) is added dropwise to a -78° C. of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]-acetic acid hydrazide (0.40 g, 1.36 mmol) in tetrahydrofuran (25 mL). The reaction mixture is stirred for 30 minutes, diluted with ethyl acetate, and washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a pale yellow oil which is crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one; mp 138.0°-140.0° C.

후처리

  1. washwashed three times with water
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a pale yellow oil which
  5. customis crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one

출처 및 근거

ORD 기록
ord-69a8454c079b4dd4bf484a5f631b85ba
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102897

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