Pyridine → 2-(1-Chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethyl pivalate

HRID 926217Notes

Reaction equation

HRID 926217 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].N1C=CC=CC=1.[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([CH3:25])[C:16]=1[CH:26]([O:29][C:30]([CH3:36])([CH3:35])[C:31]([F:34])([F:33])[F:32])[CH2:27][OH:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:3]([O:28][CH2:27][CH:26]([C:16]1[C:17]([CH3:25])=[CH:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]=1[Cl:14])[O:29][C:30]([CH3:36])([CH3:35])[C:31]([F:32])([F:33])[F:34])(=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 896766802-(1-Chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol

Product 1

HCID 896765092-(1-Chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethyl pivalate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trimethylacetyl chloride (0.17 mL, 1.36 mmol) and 4-(Dimethylamino)pyridine (55 mg, 0.45 mmol) in pyridine (2.4 mL, 29.48 mmol), 2-(1-chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol (157 mg, 0.45 mmol) in CH2Cl2 (2.4 mL) was added at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The mixture was quenched with water and concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give 2-(1-chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethyl pivalate. 1H-NMR: 400 MHz, (CDCl3) δ 8.26 (d, J=8.4 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.58-7.48 (m, 3H), 6.05 (dd, J=8.4, 5.2 Hz, 1H), 4.50 (dd, J=11.2, 8.4 Hz, 1H), 4.21 (dd, J=11.2, 4.8 Hz, 1H), 2.73 (s, 3H), 1.43 (s, 3H), 1.19 (s, 3H), 1.16 (s, 9H).

Workup

  1. customThe mixture was quenched with water
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e5358de8d771460eaf14ff083e8d0ae9
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…