Dichloromethane → Methyl 2-(cyclohexyloxy)oct-7-enoate

HRID 445403Notes

Reaction equation

HRID 445403 reaction equation
[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:3]([O:5][CH3:6])=[O:4].O1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.Cl[CH2:20]Cl>FC(F)(F)C(O)=O>[CH:14]1([O:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:3]([O:5][CH3:6])=[O:4])[CH2:20][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 86663649HCID 86663649, compound

Product 1

HCID 66822373Methyl 2-(cyclohexyloxy)oct-7-enoate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Procedure

A mixture of methyl 2-hydroxyoct-7-enoate (6.88 g, 0.040 mmol), dichloromethane (40 mL), 3,4-dihydro-2H-pyran (7.4 mL, 0.082 mol), and 6 drops of trifluoroacetic acid was stirred at room temperature overnight. The resulting mixture was concentrated in vacuo to yield methyl 2-(cyclohexyloxy)oct-7-enoate, which was used in the next step without further purification. A solution of methyl 2-(cyclohexyloxy)oct-7-enoate (500.0 mg, 1.95 mmol) dissolved in toluene (33 mL) containing 4-methyl-5-vinylthiazole (1.11 mL, 19.5 mmol) and Grubb's 2nd generation catalyst (166 mg, 0.195 mmol) was flushed with argon and heated in a sealed tube at 100° C. for 20 h. After cooling to room temperature, the solvent was removed in vacuo and the resulting residue was purified via flash silica gel chromatography (Analogix IF-280, SF25-115 g column, gradient 90:10-80:20 Heptane:EtOAc) to yield (E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate. MS (ES+) 354 (M+1).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-eaad3789f18346f6b73d99da42c2aa5e
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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