홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1-(Chloromethoxy)-2-methoxyethane → 3,7-Dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine

HRID 2395128
노트
인쇄 미리보기

반응식

HRID 2395128 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH3:21])[C:8]3[C:13]([S:14][C:15]=2[C:16]=1[CH:17]=[O:18])=[CH:12][C:11]([O:19][CH3:20])=[CH:10][CH:9]=3.[BH4-].[Li+].COC1C=CC2N(C)C3C(SC=2C=1CO)=CC(OC)=CC=3.[CH3:45][O:46][CH2:47][CH2:48][O:49][CH2:50]Cl>O1CCCC1.C([Li])CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH3:21])[C:8]3[C:13]([S:14][C:15]=2[C:16]=1[CH2:17][O:18][CH2:45][O:46][CH2:47][CH2:48][O:49][CH3:50])=[CH:12][C:11]([O:19][CH3:20])=[CH:10][CH:9]=3
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 4148881Lithium borohydrideHCID 189724883,7-Dimethoxy-10-methylphenothiazine-4-methanolHCID 189725603,7-Dimethoxy-10-methyl-phenothiazine-4-carbaldehyde

생성물 1

HCID 189725283,7-Dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine수율 84.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 178418339Butyllithium용매

실험 절차

A solution of 1.90 g (6.32 mmol) of 3,7-dimethoxy-10-methyl-phenothiazine-4-carbaldehyde in 30 ml of tetrahydrofuran was reduced with 7.6 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.1.da. The resulting 3,7-dimethoxy-10-methylphenothiazine-4-methanol was dissolved in 20 ml of tetrahydrofuran, whereupon 4.36 ml of n-butyllithium solution (1.6M in hexane) were added at -78°. The reaction mixture was brought slowly to 0°, then treated with 1.02 g (8.19 mmol) of 2-methoxy-ethoxymethyl chloride, stirred at room temperature for 2 hours and finally poured into ice-water/saturated sodium hydrogen carbonate solution. After three-fold extraction with diethyl ether the combined organic phases were washed with sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was chromatographed on silica gel with diethyl ether/hexane (3:2), whereupon 2.09 g (84.6%) of 3,7-dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine were obtained as a colourless oil.

후처리

  1. additionwere added at -78°
  2. customwas brought slowly to 0°
  3. extractionAfter three-fold extraction with diethyl ether the combined organic phases
  4. washwere washed with sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel with diethyl ether/hexane (3:2)

출처 및 근거

ORD 기록
ord-a78b4df23e11484c872b5d32c8fe6a75
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05811389

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트