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

HRID 2395128
ノート
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反応式

HRID 2395128 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 178418339Butyllithium溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a78b4df23e11484c872b5d32c8fe6a75
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05811389

反応ノート

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