3-Methylisothiazole → HCID 59556170, 화합물

HRID 1173293노트

반응식

HRID 1173293 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 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 with brine
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-872cf27573a2466597170ba95b68f55d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834021B2

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