4-Methoxybenzyl alcohol → HCID 86604216, compound

HRID 1452685Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30]([Si:34]([CH3:53])([CH3:52])[O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42](O)([C:47]([F:50])([F:49])[F:48])[C:43]([F:46])([F:45])[F:44])=[CH:38][CH:37]=1)([CH3:33])([CH3:32])[CH3:31].CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH4+].[Cl-]>C1COCC1>[C:30]([Si:34]([CH3:53])([CH3:52])[O:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:47]([F:50])([F:48])[F:49])[C:43]([F:46])([F:44])[F:45])=[CH:40][CH:41]=1)([CH3:32])([CH3:31])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4.1 g (29.6 mmol) of 4-methoxybenzyl alcohol in 100 mL of THF was added 7.76 g (29.6 mmol) of triphenylphosphine and 8.53 g (22.8 mmol) of 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol at room temperature. The reaction mixture was cooled to 0° C. and 5.7 mL (29.6 mmol) of diisopropylazo dicarboxylate were added. The solution was stirred at room temperature overnight, a solution of NH4Cl was added and the inorganic layer was extracted with ethyl acetate. The combined layers were washed with brine, and dried (Na2SO4), filtered and evaporated. Column chromatography with ethyl acetate/n-heptane 1:99 as eluent yielded 8.39 g (74%) of tert-butyl-dimethyl-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-silane as a light yellow liquid, MS: 494 (M)+.

Workup

extractionthe inorganic layer was extracted with ethyl acetate
washThe combined layers were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-baf5f7872925418b8499275d1b39bbbb
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473705B2

Reaction notes

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