Ethylene Oxide → HCID 12212449, compound

HRID 1606115Notes

Reaction equation

HRID 1606115 reaction equation
[CH2:1]1[C:4]2([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5]2)[CH2:3][O:2]1.[CH2:20]1[O:22][CH2:21]1>CO>[OH:22][CH2:21][CH2:20][N:12]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]2([CH2:3][O:2][CH2:1]2)[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6354Ethylene OxideHCID 12212448HCID 12212448, compound

Product 1

HCID 12212449HCID 12212449, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 27.5 g (0.10 mol) of 2,6,9,15,18-pentaoxa-12-azaspiro[3,15]nonadecane, 10 g (0.21 mol) of ethylene oxide and 200 ml of methanol was heated in a bomb tube at 100° for 6 hours under autogenous pressure. Solvent was evaporated, and the product was volatilized in a very short path still at 190° (~20 μ), giving 27.6 g (87%) of N-hydroxyethyl-2,6,9,15,18-pentaoxa-12-azaspiro[3.15]nonadecane as a nearly colorless oil. Ir: 2.90 (OH), 8.7-9.5 (COC, COH), 10.23 and 10.80 μ oxetane). Nmr ((CD3)2CO): 4.29 (singlet, 4, oxetane CH2), 3.74 (singlet, 4, C-CH2O), 3.6-3.3 (multiplet, 15, OCH2CH2O + OH + OCH2CH2N), 2.85-2.5 ppm (multiplet, 6, CH2N).

Workup

  1. temperaturewas heated in a bomb tube at 100° for 6 hours under autogenous pressure
  2. customSolvent was evaporated
  3. customwas volatilized in a very short path still at 190°

Sources & evidence

ORD record
ord-f644dd3e5a67410b9f6c9ab59d0a7427
Source dataset
uspto-grants-1976_04
Patent number
US03952015

Reaction notes

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