3-(1,3-benzodioxol-5-yl)prop-2-yn-1-ol → HCID 11608001, compound

HRID 1008759Notes

Reaction equation

HRID 1008759 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[C:11][CH2:12][OH:13])=[CH:9][C:4]=2[O:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[C:11][CH:12]=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 111376463-(1,3-benzodioxol-5-yl)prop-2-yn-1-ol

Product 1

HCID 11608001HCID 11608001, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1,3-benzodioxol-5-yl)prop-2-yn-1-ol (242 mg, 1.37 mmol, obtained as described in Nugent et al., 1987, J. Am. Chem. Soc., 109, 2788) in anhydrous DCM (12 mL) was added MnO2 (2.70 g, 31.1 mmol) portion wise over 2 h. The resulting mixture was stirred at rt for one additional hour, then filtered on a bed of Celite and the filtrates were evaporated under reduced pressure to give 123 mg (51%) of the title compound as a brown solid. HPLC, Rt: 2.76 min (purity: 98.9%). 1H NMR (CDCl3) δ: 9.37 (s, 1H), 7.18 (m, 1H), 7.00 (m, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.03 (s, 2H).

Workup

  1. filtrationfiltered on a bed of Celite
  2. customthe filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-8621e4d42ddc4b878576e4219ab31fc7
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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