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

HRID 2395175
Notes
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Reaction equation

HRID 2395175 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Procedure

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-methyl-phenothiazine-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.

Workup

  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)

Sources & evidence

ORD record
ord-48646b7b33ab40a2bd886ba6877fb564
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05811548

Reaction notes

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