Chloromethyl Methyl Ether → HCID 67903711, compound

HRID 1089669Notes

Reaction equation

HRID 1089669 reaction equation
[Cl:1][C:2]1[C:3]([OH:23])=[CH:4][C:5]2[CH:11]([C:12]3[C:20]4[O:19][CH2:18][CH2:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)[CH2:10][N:9]([CH3:21])[CH2:8][CH2:7][C:6]=2[CH:22]=1.[CH3:24][O:25]CCl.O1CCC[CH2:29]1>>[Cl:1][C:2]1[C:3]([O:23][CH3:29])=[CH:4][C:5]2[CH:11]([C:12]3[C:20]4[O:19][CH2:18][CH2:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)[CH2:10][N:9]([CH3:21])[CH2:8][CH:7]([O:25][CH3:24])[C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 14958952HCID 14958952, compound

Product 1

HCID 67903711HCID 67903711, compound

Conditions

Temperature
35 °C

Procedure

(+)-8-chloro-5-(2,3-dihydrobenzofuran-7-yl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (4.95 g, 0.015 mol) and potassium-tert butylate (1.85 g, 0.016 mol) are dissolved in dry tetrahydrofuran (40 ml) at 5° C. Chloromethyl methyl ether (1.51 g, 0.019 mol) is added, the temperature raising to 35° C. The reaction mixture is stirred for three hours, then evaporated to dryness under reduced pressure. The residue is partitioned between water and toluene after adjusting the pH to 8.0 by addition of 1N sodiumhydroxide. The toluene phase is dried over magnesium sulphate, and evaporated to dryness under reduced pressure. The residue is crystallized from ethylacetate (11 ml).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue is partitioned between water and toluene
  3. additionby addition of 1N sodiumhydroxide
  4. dry with materialThe toluene phase is dried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is crystallized from ethylacetate (11 ml)

Sources & evidence

ORD record
ord-c19af52e3a0642c186d1211119cbd400
Source dataset
uspto-grants-1992_01
Patent number
US05079243

Reaction notes

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