1,3-Propanediol → HCID 13764661, compound

HRID 1655933Notes

Reaction equation

HRID 1655933 reaction equation
ClC[CH2:3][O:4][CH2:5][CH3:6].[CH2:7]([OH:11])[CH2:8][CH2:9][OH:10].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:5]([O:4][CH2:3][O:10][CH2:9][CH2:8][CH2:7][OH:11])[CH3:6]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 81531Diisopropylethylamine

Product 1

HCID 13764661HCID 13764661, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of chloroethylethyl ether (50 mmol) in dry tetrahydrofuran (10 ml) was added dropwise at 0°-5° C. to a stirred solution of 1,3-propanediol (150 mmol) in dry tetrahydrofuran (100 ml) and N,N-diisopropylethylamine (75 mmol). The mixture was stirred for 2 hours at room temperature, the solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with dichloromethane:methanol (98:2) to give the title compound as a colourless oil (5.6 g, 83%); νmax (Film) 3420, 2980, 2940, 2880, 1480, 1445, 1390 and 1180 cm-1 ; δH (CDCl3) 1.20 (3H, t, J=6.5 Hz, CH3CH2), 1.8 (2H, m, CH2CH2CH2), 3.2 (1H, s, OH), 3.6 (6H, m, CH2OH, CH2O and CH3CH2), 4.8 (2H, s, OCH 2 O).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography on silica
  3. washeluting with dichloromethane:methanol (98:2)

Sources & evidence

ORD record
ord-510dedb3b74e465da7c6ef0ddd127030
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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