Methanol → 3-(4-Methoxyphenyl)-3-methylbutyronitrile

HRID 481516Notes

Reaction equation

S([CH2:11][N:12]=C=O)(C1C=CC(C)=CC=1)(=O)=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[CH:24]=O)=[CH:19][CH:18]=1.CO>COCCOC.O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[CH2:24][C:11]#[N:12])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a mixture of KOBu-t (450 mg, 4.2 mmol) and TosCH2NCO (410 mg, 2.1 mmol) in DME (8 ml) was added a solution of Compound 45 (350 mg, 2.0 mmol) in DME (2 ml) with cooling (-40° C.). The mixture was stirred at same temperature for 10 min. and then at room temperature for 1 h and to this was added MeOH (6 ml) dropwise. The mixture was stirred at same temperature for 1 hr. and then at room temperature for 15 h. The mixture was concentrated to give a solid, which was dissolved in water (10 ml). The aqueous layer was extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated in vacuo to give crude product (480 mg) as a yellow oil. The crude product was purified by a column chromatography to give Compound 46 (230 mg, 1.2 mmol,. 60%) as a colorless solid.

Workup

waitat room temperature for 1 h
stirringThe mixture was stirred at same temperature for 1 hr
waitand then at room temperature for 15 h
concentrationThe mixture was concentrated
customto give a solid, which
extractionThe aqueous layer was extracted with CH2Cl2
dry with materialThe combined extracts were dried (Na2SO4)
concentrationconcentrated in vacuo
customto give crude product (480 mg) as a yellow oil
customThe crude product was purified by a column chromatography

Sources & evidence

ORD record: ord-eb4fc9b2b2924b63954a0817e631cf3f
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789423

Reaction notes

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