Chloromethyl Methyl Ether → HCID 67903759, compound

HRID 1089671Notes

Reaction equation

HRID 1089671 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([OH:22])[C:19]([I:21])=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:24][O:25]CCl.O1CCC[CH2:29]1>>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([O:22][CH3:29])[C:19]([I:21])=[CH:20][C:15]=4[CH:14]([O:25][CH3:24])[CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 19915643HCID 19915643, compound

Product 1

HCID 67903759HCID 67903759, compound

Procedure

(+)-5-(2,3-dihydrobenzofuran-7-yl)-8-iodo-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (126.0 mg, 3.0 mmol) and potassiumm-tert-butylate 37.0 mg, 3.3 mmol) are dissolved in dry tetrahydrofuran (10 ml) at 20° C. Chloromethyl methyl ether (30.0 mg, 3.8 mmol) is added. The reaction mixture is stirred for 3.5 hours then poured into 5% sodiumhydrogencarbonate (20 ml). The product is extracted into dichloromethane (2×15 ml). The organic phase is evaporated to dryness under reduced pressure.

Workup

  1. additionthen poured into 5% sodiumhydrogencarbonate (20 ml)
  2. extractionThe product is extracted into dichloromethane (2×15 ml)
  3. customThe organic phase is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-50dfbf9efe9c4acb8b6af0b48f7034a2
Source dataset
uspto-grants-1992_01
Patent number
US05079243

Reaction notes

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