Hydrochloric Acid → HCID 59026761, compound

HRID 1025798Notes

Reaction equation

C([Mg]Cl)(C)C.I[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.[CH3:17][CH:18]([CH3:22])[C:19](=[O:21])[CH3:20].Cl>C1COCC1>[OH:21][C:19]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)([CH3:20])[CH:18]([CH3:22])[CH3:17]

Participants

Conditions

Temperature: -40 °C

Procedure

Isopropyl magnesium chloride (12.0 mL of a 2 M solution in THF, 24.0 mmol) was added to a solution of methyl 4-iodobenzoate (5.24 g, 20.0 mmol) in THF (50 mL) at −40° C. After 1 h, a second portion of isopropyl magnesium chloride (5.00 ml, of a 2 M solution in THF, 10.0 mmol) was added and the resulting mixture allowed to stir at −40° C. for 4 h. 3-Methyl-2-butanone (2.10 mL, 19.6 mmol) was then added and the resulting mixture allowed to warm to room temperature overnight. The reaction mixture was poured into 1 N HCl and extracted three times with EtOAc. The combined organic extracts were washed water, brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent) afforded the title compound i-2a. 1HNMR (500 MHz, CDCl3): δ 8.02 (d, 2H, J=8.5 Hz), 7.52 (d, 2H, J=8.5 Hz), 3.95 (s, 3H), 2.05 (p, 1H, J=6.6 Hz), 1.57 (s, 3H), 0.95 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.9 Hz).

Workup

temperatureto warm to room temperature overnight
extractionextracted three times with EtOAc
washThe combined organic extracts were washed water, brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent)

Sources & evidence

ORD record: ord-6e63a995a95e4578a6fe16efa2d6ff85
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729104B2

Reaction notes

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