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

HRID 342199노트

반응식

HRID 342199 반응식
[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

참가 물질

10

반응물 6

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4c99b9643117459f8cdb4bef669e8787
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856503

반응 노트

불러오는 중…