Ammonium Chloride → 1-(6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylyl)prop-2-yn-1-ol

HRID 2377200Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([CH:22]=[O:23])=[CH:11][C:10]=1[C:24]([CH3:27])([CH3:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([Mg]Br)#[CH:29].[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:13][C:12]([CH:22]([OH:23])[C:28]#[CH:29])=[CH:11][C:10]=1[C:24]([CH3:27])([CH3:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

780 mg (2.2 mmol) of 6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylcarbaldehyde are dissolved in 50 mL of THF, and the reaction medium is cooled to 0° C. 5.7 mL (2.8 mmol) of 0.5 M ethynylmagnesium bromide solution are added slowly. The medium is stirred at 0° C. for 2 hours and the reaction is then treated with a saturated ammonium chloride solution. The residue obtained is purified by chromatography on a column of silica (eluent: 9 heptane/1 ethyl acetate). A yellow oil is obtained (m=740 mg; yield=89%).

Workup

customThe residue obtained
customis purified by chromatography on a column of silica (eluent: 9 heptane/1 ethyl acetate)
customA yellow oil is obtained (m=740 mg; yield=89%)

Sources & evidence

ORD record: ord-88d41b50658a42c0b8887c92d399ce81
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468457B2

Reaction notes

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