HCID 86603460, compound → HCID 86603463, compound

HRID 1171013Notes

Reaction equation

[CH3:1][C:2]1[C:3](I)=[C:4]([OH:23])[CH:5]=[C:6]([CH3:22])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[C:11]([CH:19]([CH3:21])[CH3:20])[CH:10]=1>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[C:11]([CH:19]([CH3:21])[CH3:20])[CH:10]=2)=[C:6]([CH3:22])[CH:5]=[C:4]([OH:23])[C:3]=1[C:16]([O:15][CH3:12])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3,5-dimethyl-2-iodo-4-(4′-methoxymethoxy-3′-iso-propylbenzyl)phenol (compound 47, step a; 1.0 g, 2.27 mmol) and PdCl2(PPh3)2 (0.10 g, 0.14 mmol) in TEA (1.6 mL) and methanol (8.0 mL) was heated under a CO atmosphere (60 psi) at 80° C. for 72 h. The reaction mixture was cooled to room temperature and filtered through a Celite plug. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel, eluting with 10% ethyl acetate in hexanes to afford methyl 2,4-dimethyl-6-hydroxy-3-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzoate (0.32 g, 38%): 1H NMR (300 MHz, CD3OD): δ 6.93 (m, 2 H), 6.67 (s, 2 H), 5.18 (s, 1 H), 3.98 (s, 2 H), 3.92 (s, 3 H), 3.48 (s, 3 H), 3.30 (m, 1 H), 2.22 (m, 6 H), 1.18 (d, J=6.9 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:5); Rf=0.60.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a Celite plug
customThe solvent was removed under reduced pressure
customthe crude product was purified by column chromatography on silica gel
washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b9ff95aada43441fa833f71c047d1482
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829552B2

Reaction notes

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