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Tetrahydrofuran → Ethyl 4-cyano-4-(3,4-dichlorophenyl)-6-(t-butyldimethylsilyloxy)hexanoate

HRID 323251
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HRID 323251 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C(OCC)(=O)C.CCCCCC.O>[C:10]([C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])#[N:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 68320Ethyl 3-bromopropionateHCID 2733832Lithium HexamethyldisilazideHCID 184647992-(3,4-Dichlorophenyl)-4-(t-butyldimethylsilyloxy)butyronitrile

생성물 1

HCID 18464536Ethyl 4-cyano-4-(3,4-dichlorophenyl)-6-(t-butyldimethylsilyloxy)hexanoate

시약·촉매·용매 2

HCID 962
Water
용매
HCID 21226206Ethyl acetate hexane용매

실험 절차

Combine 2-(3,4-dichlorophenyl)-4-(t-butyldimethylsilyloxy)butyronitrile (13.35 g, 38.8 mmol) and anhydrous tetrahydrofuran (50 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of lithium bis(trimethylsilyl)amide (42.6 mL, 1 M in THF, 42.6 mmol). Add dropwise, ethyl 3-bromopropionate (7.71 g, 42.6 mmol). Warm the reaction mixture to ambient temperature. After 18 hours, add water. Separate the aqueous layer and extract three times with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 90% ethyl acetate/hexane to give the title compound: Rf=0.35 (silica gel, 10% ethyl acetate/hexane).

후처리

  1. temperatureCool in a dry-ice/acetone bath
  2. additionAdd dropwise
  3. customSeparate the aqueous layer
  4. extractionextract three times with ethyl acetate
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

출처 및 근거

ORD 기록
ord-bf1ee93cd3fa473ea644a895aa58d37d
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211199B1

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