N-[1-[(octadecyloxy)methyl]-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide → N-[1-(Hydroxymethyl)-2-(octadecyloxy)ethyl]acetamide

HRID 235713Notes

Reaction equation

HRID 235713 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([NH:30][C:31](=[O:33])[CH3:32])[CH2:22][O:23]C1CCCCO1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CO.Cl>[OH:23][CH2:22][CH:21]([NH:30][C:31](=[O:33])[CH3:32])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 20218649N-[1-[(octadecyloxy)methyl]-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide

Product 1

HCID 19829267N-[1-(Hydroxymethyl)-2-(octadecyloxy)ethyl]acetamideYield 83.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of about 4.69 g of N-[1-[(octadecyloxy)methyl]-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide in about 200 ml of methanol and about 4 ml of about 1N hydrochloric acid was stirred for about 24 hours and the methanol removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, dried and the solvent removed, giving about 3.2 g of the desired title compound, mp 82°-85° C.

Workup

  1. customthe methanol removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-8478c2d457434ff6a83e883a6e38c73a
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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