4-(Methoxymethoxy)benzaldehyde → (2,6-Dimethyl-4-triisopropylsilanyloxyphenyl)-(4-methoxymethoxyphenyl)methanol

HRID 1170992Notes

Reaction equation

Br[C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:20].C([Li])CCC.[CH3:26][O:27][CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1>C1COCC1.C(OCC)(=O)C.O>[CH3:20][C:3]1[CH:4]=[C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:17]=[C:18]([CH3:19])[C:2]=1[CH:34]([C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:28][O:27][CH3:26])=[CH:37][CH:36]=1)[OH:35]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (4-bromo-3,5-dimethyl-phenoxy)triisopropylsilane (8.0 g, 23.30 mmol) in THF (50 mL) was added a solution of n-butyllithium (2.5 M in THF, 90 mL) at −78° C. The heterogeneous mixture was stirred at −78° C. for 1 h A solution of 4-methoxymethoxy-benzaldehyde (3.09 g, 18.58 mmol) in THF (5 mL) was added and the mixture was stirred at −78° C. for 1 h then warmed up to r.t. The reaction was then diluted with ethyl acetate and water, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated to afford crude (2,6-dimethyl-4-triisopropylsilanyloxyphenyl)-(4-methoxymethoxyphenyl)methanol. Carried on to the next step without further purification.

Workup

additionwas added
temperaturethen warmed up to r.t
customthe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-55397d3f68fc49dbb85d0bc90262c3f4
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829552B2

Reaction notes

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