Ethylene Glycol → HCID 12669329, compound

HRID 223236Notes

Reaction equation

HRID 223236 reaction equation
Br[CH2:2][C:3]1[O:4][CH:5]=[CH:6][CH:7]=[C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=12.C(N(C(C)C)CC)(C)C.[CH2:27]([OH:30])[CH2:28][OH:29]>>[CH3:15][O:14][C:12]1[C:11]([O:16][CH3:17])=[CH:10][C:9]2[CH:3]([CH2:2][O:29][CH2:28][CH2:27][OH:30])[O:4][CH2:5][CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 81531DiisopropylethylamineHCID 20522892HCID 20522892, compound

Product 1

HCID 12669329HCID 12669329, compoundYield 89%

Procedure

A mixture of 3.67 g (12.2 mmoles) of 1-bromomethyl-7,8-dimethoxy-2-benzoxepin, 2.12 ml (12.2 mmoles) of diisopropylethylamine, and 15 ml of ethylene glycol is heated at 100° for 7 hours. The reaction mixture is then cooled and extracted with methylene chloride, then with water and finally with brine. The organic layer is filtered through Na2SO4, taken to dryness, and chromatographed on silica gel to give 3.06 g (89%) of 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethanol: mass spectrum: M+ (m/e=282).

Workup

  1. temperatureis heated at 100° for 7 hours
  2. temperatureThe reaction mixture is then cooled
  3. extractionextracted with methylene chloride
  4. filtrationThe organic layer is filtered through Na2SO4
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-87472d4865bd4a4d8c6959c3c59e25e4
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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