Diisopropylamine → (RS)-3-(2-hydroxy-4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-ol

HRID 342199ノート

反応式

HRID 342199 の反応式
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[S:4][N:3]=1.[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.C([Li])CCC.[CH3:32][C:33]([CH3:37])=[CH:34][CH:35]=[O:36].C(=O)([O-])O.[Na+]>C1COCC1.CCOCC.C(O)(=O)C>[OH:36][CH:35]([CH:34]=[C:33]([CH3:37])[CH3:32])[CH2:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[S:4][N:3]=1

参加物

10

反応物 6

HCID 7912DiisopropylamineHCID 610203-Methyl-2-butenalHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 1357420033-Methylbenzo[d]isothiazol-6-olHCID 178418339Butyllithium

生成物 1

HCID 136365324(RS)-3-(2-hydroxy-4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-ol

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

1.5 g of 3-methyl-benzo[d]isothiazol-6-ol in 26 ml of THF are added to a LDA solution previously prepared from 3.9 ml of diisopropylamine and 16.0 ml of n-butyllithium (1.6M in hexane) in 23 ml of THF and the mixture is stirred at -78° C. 2.5 ml of 3-methyl-2-butenal in 40 ml of THF are added. The reaction mixture is thawed overnight and neutralized with 3.9 ml of acetic acid in 20 ml of ether. The mixture is added to sodium hydrogen carbonate solution, the inorganic phase is extracted with ethyl acetate and the organic phases are washed with sodium chloride solution and dried. The crude product is purified by chromatography (silica gel, ethyl acetate:hexane 1:1). 1.5 g of (RS)-3-(2-hydroxy-4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-ol are obtained.

後処理

  1. extractionthe inorganic phase is extracted with ethyl acetate
  2. washthe organic phases are washed with sodium chloride solution
  3. customdried
  4. customThe crude product is purified by chromatography (silica gel, ethyl acetate:hexane 1:1)

出典と根拠

ORDレコード
ord-4c99b9643117459f8cdb4bef669e8787
出典データセット
uspto-grants-1999_01
特許番号
US05856503

反応ノート

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