3-Methylisothiazole → HCID 59556170, 화합물

HRID 1025795노트

반응식

HRID 1025795 반응식
C([Li])CCC.[CH3:6][C:7]1[CH:11]=[CH:10][S:9][N:8]=1.[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1>CCCCCC.O1CCCC1>[CH3:6][C:7]1[CH:11]=[C:10]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:17][CH2:18]2)[S:9][N:8]=1

참가 물질

6

반응물 3

HCID 127473-MethylisothiazoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

생성물 1

HCID 59556170HCID 59556170, 화합물수율 70.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

At −78° C., 1.5 M of n-butyllithium in hexane (6.7 mL) was slowly added to a solution of 3-methylisothiazole (1.0 g, 0.010 mol) in tetrahydrofuran (15 mL) over a period of 20 min. After being stirred for another 30 min, 1,4-dioxa-spiro[4.5]decan-8-one (1.56 g, 0.00999 mol) in tetrahydrofuran (5 mL) was added within 10 min. The reaction mixture was stirred for another 2 hour at −78° C. and allowed to warm up overnight to room temperature. After quenching with brine, the mixture was extracted with EtOAc. The organic layer was dried and concentrated. Chromatography on silica gel eluting with hexane/EtOAc (1:5˜1:1) provided 1.8 g (70.6%) of the title compound. MS (M+H)+ 256.

후처리

  1. stirringThe reaction mixture was stirred for another 2 hour at −78° C.
  2. temperatureto warm up overnight to room temperature
  3. customAfter quenching with brine
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ac444c1153ca42ee853b603cdc3145ac
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729063B2

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