Water → HCID 21896322, compound

HRID 719065Notes

Reaction equation

HRID 719065 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:19]([O:11][C:6]1([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:22])[CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 21896329HCID 21896329, compound

Product 1

HCID 21896322HCID 21896322, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

In 80 ml of toluene were dissolved 16.8 g of 1-(2-tetrahydrofuranyl)cyclopentanol, 13.1 g of triethylamine, and 0.5 g of 4-(N,N-dimethylamino)pyridine. Then 10.7 g of acrylic chloride was added to the solution at 50° C., which was stirred at the temperature for one hour. Water, 50 ml, was added to the solution below 30° C., followed by ordinary post-treatment. Vacuum distillation yielded 18.1 g of 1-(2-tetrahydrofuranyl)cyclopentyl acrylate. The two-step yield was 80%.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-6c96688532d64bd9965f51e641825fea
Source dataset
uspto-grants-2006_11
Patent number
US07132215B2

Reaction notes

Loading…