Triphenylphosphine → Methyl 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[(2-methylphenyl)methyl]oxy}benzoate

HRID 1510297Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:54][O:55][CH2:56][C@H:57](O)[CH3:58]>ClC>[CH3:54][O:55][CH2:56][C@@H:57]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:58]

Participants

Conditions

Temperature: 2.5 °C

Procedure

A stirred suspension of methyl 3-hydroxy-5-{[(2-methylphenyl)methyl]oxy}benzoate (15.3 g, 56.25 mmol) and triphenyl phosphine (14.4 g, 55 mmol) in dry chloromethane (900 ml) was cooled in an ice-bath and diisopropyl azodicarboxylate (11.88 ml, 55 mmol) was added dropwise. The reaction mixture was stirred at 0-5° C. for 30 minutes and (R)-methoxy-propan-2-ol was added dropwise. The reaction mixture was stirred at ambient temperature for 16 hours, and filtered through diatomaceous earth. The filtrate was evaporated and purified by column chromatograph on silica gel eluting with 10% ethyl acetate in iso-hexane to give the desired compound (10.7 g, 55%).

Workup

temperaturewas cooled in an ice-bath
stirringThe reaction mixture was stirred at ambient temperature for 16 hours
filtrationfiltered through diatomaceous earth
customThe filtrate was evaporated
custompurified by column chromatograph on silica gel eluting with 10% ethyl acetate in iso-hexane

Sources & evidence

ORD record: ord-d9c5d47402df41ab805850d24b6376ce
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211925B2

Reaction notes

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