2-Methyl-3-butyn-2-ol → 4-(3-(3-Hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol

HRID 454353Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]([OH:17])([C:15]#[CH:16])[CH3:14]>C(N(CC)CC)C.[Cu]I>[OH:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([C:16]#[C:15][C:13]([CH3:14])([OH:17])[CH3:12])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a degassed solution of 3-(3-bromophenyl)propan-1-ol (8) (0.95 g, 4.5 mmol) and 2-methyl-3-butyn-2-ol (9) (1.6 mL, 16 mmol) in triethylamine (25 mL) was added PdCl2(PPh3)3 (0.095 g, 0.14 mmol) and CuI (0.027 g, 0.14 mmol) The resulting mixture was degassed and stirred under argon at 70° C. for 15 h. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc (50 mL). The solution was filtered through filter paper, washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (10 to 100% EtOAc-hexanes gradient) gave 4-(3-(3-hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol (10) as a light brown oil: Yield (0.78 g, 80%): 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.18 (m, 4H), 5.46 (s, 1H), 4.48 (t, J=5.2 Hz, 1H), 3.38 (q, J=6.0 Hz, 2H), 2.59 (t, J=7.2 Hz, 2H), 1.66-1.73 (m, 2H), 1.46 (s, 6H).

Workup

customwas degassed
concentrationThe reaction mixture was concentrated under reduced pressure
additiondiluted with EtOAc (50 mL)
filtrationThe solution was filtered
filtrationthrough filter paper
washwashed with water (50 mL) and brine (50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customPurification by flash chromatography (10 to 100% EtOAc-hexanes gradient)

Sources & evidence

ORD record: ord-1b28d3f5702d48e8988abbe9c1d02714
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492589B2

Reaction notes

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