HCID 67373277, compound → HCID 67418235, compound

HRID 1805913Notes

Reaction equation

HRID 1805913 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[C:17][CH2:18][OH:19])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]>[Pd].CCOC(C)=O>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:12](/[CH:16]=[CH:17]\[CH2:18][OH:19])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 67373277HCID 67373277, compound

Product 1

HCID 67418235HCID 67418235, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 2-(acetyloxy)-5-(3-hydroxyprop-1-yn-1-yl)-3-methylbenzoate (0.417 g, 1.590 mmol) and palladium on carbon (170 mg, 1.597 mmol) in EtOAc (20 mL) was stirred at room temperature under a balloon atmosphere of H2 for 3 days. The reaction mixture was filtered through a plug of Celite and washed through with EtOAc (3×30 mL). The filtrate was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 0-20% EtOAc in hexanes over 40 min) to afford methyl 2-(acetyloxy)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-3-methylbenzoate, as a pale yellow oil. 1H NMR (500 MHz, CHCl3): δ 7.69 (s, 1 H); 7.29 (s, 1 H); 6.53 (d, J=12 Hz, 1 H); 5.94 (m, 1 H); 4.44 (d, J=6.4 Hz, 2 H); 3.88 (s, 3 H); 2.40 (s, 3 H); 2.25 (s, 3 H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washwashed through with EtOAc (3×30 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give the crude product
  5. customThis was purified by flash chromatography (Si, 0-20% EtOAc in hexanes over 40 min)

Sources & evidence

ORD record
ord-d3002dae82714dd9801c09b0f0d68747
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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