3-Methylisothiazole → HCID 59556170、化合物

HRID 1173293ノート

反応式

HRID 1173293 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 59556170HCID 59556170、化合物収率 70.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-872cf27573a2466597170ba95b68f55d
出典データセット
uspto-grants-2010_11
特許番号
US07834021B2

反応ノート

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