Dansyl chloride → HCID 86614223, compound

HRID 1746080Notes

Reaction equation

HRID 1746080 reaction equation
[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.[S:18](Cl)([C:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[C:26]([N:27]([CH3:29])[CH3:28])[C:25]=2[CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19]>C(Cl)Cl>[C:1]([O:5][CH2:6][CH2:7][O:8][S:18]([C:21]1[C:33]2[C:25](=[C:26]([N:27]([CH3:29])[CH3:28])[CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11801Dansyl chlorideHCID 131652-Hydroxyethyl acrylateHCID 81531Diisopropylethylamine

Product 1

HCID 86614223HCID 86614223, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxyethyl acrylate (25.8 mg, 0.2 mmol) in 2 ml of freshly distilled CH2Cl2 was added diisopropylethylamine (DIPEA, 0.35 ml, 0.2 mmol) dropwise at 0° C. Dansyl chloride (50.0 mg, 0.19 mmol) was then added dropwise, and 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 extracted (3×20 ml) with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 37.5 mg (56%) of 2-(5-dimethylamino-naphthalene-1-sulfonyloxy)-ethyl acrylate as a yellow semi solid. 1H NMR (250 MHz) δ 8.61 (d, J=8.6 Hz, 1H), 8.26 (t, J=6.3 Hz, 2H), 7.56 (m, 2H), 7.20 (d, J=7.7 Hz, 1H), 6.19 (dd, J=16.5, 2.5 Hz, 1H), 5.80 (dd, J=16.5, 10.3 Hz, 1H), 5.71 (dd, J=16.5, 10.3 Hz, 1H), 4.25 (m, 4H), 2.88 (s, 6H). 13C NMR (63 MHz) δ 158.0, 151.7, 131.8, 131.5, 130.9, 130.6, 129.8, 128.8, 127.3, 123.0, 119.4, 115.6, 67.8, 61.5, 45.4.

Workup

  1. customThe reaction was quenched with a 5% solution of NH4Cl
  2. extractionextracted (3×20 ml) with CH2Cl2
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. custompurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

Sources & evidence

ORD record
ord-06120a6b1a444b4998f7573bd30c757a
Source dataset
uspto-grants-2015_10
Patent number
US09149440B2

Reaction notes

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