Triethylamine → 2-(2-Oxo-1,3,2-dioxaphospholan-2-yloxy)ethyl acrylate

HRID 725190Notes

Reaction equation

HRID 725190 reaction equation
[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.Cl[P:17]1(=[O:22])[O:21][CH2:20][CH2:19][O:18]1>C(OCC)C>[C:1]([O:5][CH2:6][CH2:7][O:8][P:17]1(=[O:22])[O:21][CH2:20][CH2:19][O:18]1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131652-Hydroxyethyl acrylateHCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxide

Product 1

HCID 135907382-(2-Oxo-1,3,2-dioxaphospholan-2-yloxy)ethyl acrylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

2-Hydroxyethyl acrylate (11.5 ml, 0.1M) and triethylamine (14.6 ml) in dry diethyl ether (250 ml) were cooled to -25° C. under nitrogen as a solution of 2-chloro-2-oxo-1,3,2-dioxaphospholane (14.3 g) in dry diethyl ether was added over 20 minutes. The mixture was stirred for a further 1 hour at -20° C. and then allowed to warm to 10° C. over a further hour. The precipitate was filtered, washed with ethyl acetate (100 ml) and the combined filtrate and washings evaporated under reduced pressure to give a pale yellow oil (21 g).

Workup

  1. additionwas added over 20 minutes
  2. temperatureto warm to 10° C. over a further hour
  3. filtrationThe precipitate was filtered
  4. washwashed with ethyl acetate (100 ml)
  5. customthe combined filtrate and washings evaporated under reduced pressure

Sources & evidence

ORD record
ord-14df61bd1bba4ba7badf6cec3d4027c8
Source dataset
uspto-grants-1998_01
Patent number
US05705583

Reaction notes

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