Propionyl chloride → HCID 67144739, compound

HRID 1992571Notes

Reaction equation

HRID 1992571 reaction equation
O[C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[CH:3]=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>>[C:17]([C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[CH:3]=1)(=[O:20])[CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 62324Propionyl chlorideHCID 1355380184-hydroxy-5-Methyl-5-octylthiophen-2(5H)-one

Product 1

HCID 67144739HCID 67144739, compoundYield 48.1%

Procedure

From 32 (40 mg, 0.17 mmol) and propionyl chloride (20 μL, 0.22 mmol) following general procedure K was obtained 64 (23.1 mg, 47%) after flash chromatography (15% EtOAc/Hexanes). 1H NMR (300 MHz, CDCl3) δ 0.85 (t, J=7 Hz, 3H), 1.12-1.25 (m, 13H), 1.42-1.49 (m, 2H), 1.64 (s, 3H), 1.78-1.84 (m, 2H), 2.57 (q, J=7.5 Hz, 2H), 6.39 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 8.71, 14.0, 22.6, 25.1, 25.9, 27.9, 29.1, 29.3, 29.5, 31.8, 38.6, 60.4, 113.8, 169.1, 177.0, 179.9. IR (NaCl) 2928, 1787, 1688 cm−1; Analysis Calculated for C16H26O3S: C, 64.4; H, 8.78; Found: C, 64.3; H, 8.89.

Sources & evidence

ORD record
ord-fcfafa5a2a0741e3a7e826695cf80633
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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