Methyl chloroformate → HCID 135471195, compound

HRID 1992573Notes

Reaction equation

HRID 1992573 reaction equation
[OH:1][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.Cl[C:18]([O:20][CH3:21])=[O:19].CN(C1C=CC=CN=1)C.CCN(CC)CC>CCOC(C)=O>[CH3:21][O:20][C:18]([C:3]1[C:4](=[O:16])[S:5][C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:2]=1[OH:1])=[O:19]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 1355380184-hydroxy-5-Methyl-5-octylthiophen-2(5H)-one

Product 1

HCID 135471195HCID 135471195, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 32 (91 mg, 0.37 mmol), methyl chloroformate (63 μL, 0.81 mmol), dimethylaminopyridine (DMAP) (23 mg, 0.18 mmol) and NEt3 (108 μL, 0.77 mmol) following General Procedure L was obtained 70 (66 mg, 59%, 79% based on recovered starting material) after flash chromatography (30% EtOAc/2% AcOH/Hexanes-10% THF/2% AcOH/EtOAc). 1H NMR (300 MHz, MeOD) δ 0.86 (t, J=6.9 Hz, 3H), 1.20 (bs, 12H), 1.35 (s, 3H), 1.55 (m, 1H), 1.71-1.75 (m, 1H), 3.59 (s, 3H); 13C NMR (75 MHz, MeOD) δ 13.3, 21.8, 24.4, 27.0, 28.5, 28.6, 29.0, 30.2, 31.0, 50.4, 58.3, 124.6, 168.1, 187.7, 196.7. HRMS (EI) m/z calculated for C15H24O4S+) 300.1389 obsd. 300.1375.

Sources & evidence

ORD record
ord-5e02b12bfc054306b7f232c8c301932f
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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