HCID 67418235, compound → HCID 67379178, compound

HRID 1805914Notes

Reaction equation

HRID 1805914 reaction equation
[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]>[Pd].CCOC(C)=O>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][CH2:17][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 67418235HCID 67418235, compound

Product 1

HCID 67379178HCID 67379178, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% palladium on carbon (146 mg, 0.137 mmol) in a solution of methyl 2-(acetyloxy)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-3-methylbenzoate (362 mg, 1.370 mmol) in EtOAc (17.2 mL) was shaken in a Parr shaker under H2 at 40 psi overnight. The reaction mixture was filtered through a plug of Celite and washed through with EtOAc. The filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 60% EtOAc in hexanes over 1125 mL) to afford methyl 2-(acetyloxy)-5-(3-hydroxypropyl)-3-methylbenzoate, as a colorless oil. LCMS calc.=289.1; found=288.9 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 7.65 (d, J=2.2 Hz, 1 H); 7.25 (d, J=2.2 Hz, 1 H); 3.84 (s, 3 H); 3.64 (t, J=6.4 Hz, 2 H); 2.67 (t, J=7.8 Hz, 2 H); 2.35 (s, 3 H); 2.18 (s, 3 H); 1.89-1.82 (m, 2 H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washwashed through with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford the crude product
  5. customThis was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 60% EtOAc in hexanes over 1125 mL)

Sources & evidence

ORD record
ord-63e238b594394f979987d6378762df91
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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