2,2-Dimethylbutyryl chloride → HCID 14403853, compound

HRID 1194139Notes

Reaction equation

HRID 1194139 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3](Cl)=[O:4].[CH3:9][C:10]1([CH3:37])[CH2:15][O:14][CH:13](/[CH:16]=[CH:17]/[C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[OH:27])[O:12][CH2:11]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:9][C:10]1([CH3:37])[CH2:11][O:12][CH:13](/[CH:16]=[CH:17]/[C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH:26]([O:27][C:3](=[O:4])[C:2]([CH3:8])([CH3:1])[CH2:6][CH3:7])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[O:14][CH2:15]1

Participants

5

Reactant 2

HCID 799582,2-Dimethylbutyryl chlorideHCID 14403850HCID 14403850, compound

Product 1

HCID 14403853HCID 14403853, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethylbutyryl chloride (1.2 mL, 8.66 mmol) and 4-dimethylaminopyridine (1.17 g, 9.58 mmol) were added under a nitrogen atmosphere at room temperature to a solution of the alcohol prepared in the preceding paragraph (880 mg, 2.18 mmol) in 50 mL of methylene chloride. After the addition, the solution was stirred at room temperature for 5 hours. The solution was washed with 10% HCl, 10% NaHCO3, dried (anh. K2CO3) and the solvent removed under reduced pressure. Purification of the residual oil on silica gel (230-400 mesh) using 4:1 methylene chloride:hexane as an eluent gave 2,2-dimethylbutanoic acid (E)-1-[2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)-ethenyl]-3,5-dimethylphenyl]decyl ester as an oil (960 mg, 88%): IR (film) 2910, 2840 and 1720 cm-1 ; NMR (DMSO-d6) δ 0.66-0.78 (6H, m), 0.86 (3H, t, J=9 Hz), 1.02-1.20 (9H, m), 1.20-1.40 (14H, m), 1.50-1.70 (2H, m), 2.20 (3H, s), 2.24 (3H, s), 3.56 (2H, d, J=10 Hz), 3.64 (2H, d, J=10 Hz), 5.10 (1H, d, J=4 Hz), 5.68 (1H, dd, J=4, 15 Hz), 5.74-5.84 (1H, m), 6.78 (1H, d, J=15 Hz), 6.98 (2H, s).

Workup

  1. additionAfter the addition
  2. washThe solution was washed with 10% HCl, 10% NaHCO3
  3. dry with materialdried (anh. K2CO3)
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residual oil on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-ae7562a61ed64f439cc4ae53cce1a564
Source dataset
uspto-grants-1989_03
Patent number
US04812583

Reaction notes

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