Acetic Anhydride → (2E)-3-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-enyl acetate

HRID 2078452Notes

Reaction equation

HRID 2078452 reaction equation
[CH:1]([O:4][C:5]1[CH:21]=[CH:20][C:8]([O:9][C:10]2[S:11][C:12](/[CH:15]=[CH:16]/[CH:17]([OH:19])[CH3:18])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30]>ClCCl.CN(C)C1C=CN=CC=1>[C:29]([O:19][CH:17]([CH3:18])/[CH:16]=[CH:15]/[C:12]1[S:11][C:10]([O:9][C:8]2[CH:20]=[CH:21][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[CH:6][CH:7]=2)=[N:14][CH:13]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67096817(3E)-4-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]but-3-en-2-ol

Product 1

HCID 67096975(2E)-3-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-enyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 7D (200 mg, 0.65 mmole) in dichloromethane (10 mL) at room temperature, was added triethylamine (750 μL) followed by acetic anhydride (300 μL, 3.2 mmole) and 4-(dimethylamino)pyridine (5 mg). The reaction mixture was stirred at room temperature, overnight and quenched with methanol for an hour. The solvent was evaporated in vacuum and the product was purified via silica column, using a gradient of 5-20% ethyl acetate in hexane. Yield of the clear oil, 165 mg (72.5%). 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=6.25 Hz, 6H) 1.35 (d, J=6.62 Hz, 3H) 2.06 (s, 3H) 4.40-4.63 (m, 1H) 5.35-5.50 (m, 1H) 5.73 (dd, J=15.81, 6.62 Hz, 1H) 6.57 (d, J=15.81 Hz, 1H) 6.84-6.96 (m, 2H) 7.07 (s, 1H) 7.12-7.22 (m, 2 H). Mass spectrum DCI 348 (M+H)+.

Workup

  1. customquenched with methanol for an hour
  2. customThe solvent was evaporated in vacuum
  3. customthe product was purified via silica column

Sources & evidence

ORD record
ord-58fc3056c23a42169cd58458190797a3
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Reaction notes

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