1,2-Dichloroethane → HCID 69446413, compound

HRID 1746081Notes

Reaction equation

HRID 1746081 reaction equation
[C:1]([O:5][CH2:6][CH2:7]O)(=[O:4])[CH:2]=[CH2:3].[C:9]1([C:19]([OH:21])=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][CH:6]([O:20][C:19]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:21])[CH3:7])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 68471-Naphthoic acidHCID 131652-Hydroxyethyl acrylate

Product 1

HCID 69446413HCID 69446413, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxyethyl acrylate (1.01 g, 8.7 mmol) and 1-naphthoic acid (1.00 g, 5.8 mmol) in 10 ml of freshly distilled CH2Cl2 was added EDC (1.60 g, 8.7 mmol) and DMAP (cat. amount) at room temperature. The resultant mixture was stirred at room temperature until TLC indicated the disappearance of starting material. The reaction was quenched with a 5% solution of NH4Cl and the mixture was washed with water. After extraction with EtOAc (3×20 ml), the organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 1.29 g (82%) of naphthalene-1-carbonyloxy-2-ethyl acrylate as a colorless oil. 1H NMR (250 MHz) δ 8.91 (d, J=8.4 Hz, 1H), 8.21 (d, J=7.1 Hz, 1H), 8.04 (d, J=8.2 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.57 (m, 3H), 6.49 (d, J=17.3 Hz, 1H), 6.19 (dd, J=17.3, 10.4 Hz, 1H), 5.71 (d, J=10.4 Hz, 1H), 4.66 (m, 2H), 4.58 (m, 2H). 13C NMR (63 MHz) δ 167.2, 165.9, 133.8, 133.6, 131.5, 131.3, 130.5, 128.6, 128.0, 127.8, 126.6, 126.2, 125.7, 124.5, 62.7, 62.3.

Workup

  1. customThe reaction was quenched with a 5% solution of NH4Cl
  2. washthe mixture was washed with water
  3. extractionAfter extraction with EtOAc (3×20 ml)
  4. dry with materialthe organic layers were dried over anhydrous MgSO4
  5. custompurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

Sources & evidence

ORD record
ord-ff809e820ab34e89ae257f8a178eb9b0
Source dataset
uspto-grants-2015_10
Patent number
US09149440B2

Reaction notes

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