Water → 2-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene

HRID 129930노트

반응식

HRID 129930 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH:14]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH2:13][CH2:12]2.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26].O>C1COCC1>[CH2:18]([N:17]([CH2:21][CH2:22][CH3:23])[CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([Sn:25]([CH3:27])([CH3:26])[CH3:24])[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)[CH2:19][CH3:20]

참가 물질

6

반응물 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 194270892-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene수율 152.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Butyllithium (1.2M in hexane; 2.8 ml; 3.4 mmol) was added to a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (1 g; 3.22 mmol) in THF (50 ml) at -78° C. After 1.5 hr., a solution of trimethyltin chloride (1.3 g, 2.0 mmol) in THF (20 ml) was added. The reaction mixture was allowed to warm to room temperature, stirred overnight at room temperature, poured into water, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product. Purification by chromatography using 1:10 methanol:methylene chloride gave 1.2 g of the desired product which was used directly in the next step.

후처리

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by chromatography

출처 및 근거

ORD 기록
ord-0f89195b860b4650ac558c089368650d
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470977

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