tert-Butyldimethylsilyl chloride → HCID 68588684, compound

HRID 1967641Notes

Reaction equation

[Si:1](OC[C@@H](C1C=CC(B(O)O)=CC=1C)C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([CH3:32])[CH2:30][OH:31])=[C:25]([O:33][CH3:34])[CH:24]=1.C([Si](C)(C)Cl)(C)(C)C>>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([CH3:32])[CH2:30][O:31][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:25]([O:33][CH3:34])[CH:24]=1

Participants

Reactant 3

HCID 28928tert-Butyldimethylsilyl chloride

HCID 59315029HCID 59315029, compound

HCID 68590565HCID 68590565, compound

Product 1

HCID 68588684HCID 68588684, compoundYield 81%

Procedure

Using procedure analogous to that used to prepare Intermediate 10, Intermediate 9 (7.8 g, 158 mmol) was protected with tert-Butyldimethylchlorosilane to yield (R)-(2-(4-bromo-2-methoxyphenyl)propoxy)(tert-butyl)dimethylsilane (9.2 g, 81% yield) as a clear oil. The protected alcohol (3.00 g, 8.35 mmol) was reacted with BuLi and trimethyl borate to yield Intermediate 10 (1.87 g, 5.77 mmol, 69.1% yield) as a colorless oil. 1H NMR (400 MHz, methanol-d3) 8 ppm 7.12-7.19 (m, 2H) 7.12 (s, 1H) 3.82 (s, 3H) 3.75 (dd, J=9.89, 5.50 Hz, 1H) 3.52-3.58 (m, 0H) 3.32-3.37 (m, 0H) 1.23 (d, J=6.60 Hz, 3H) 0.84 (s, 9H) −0.04 (d, J=2.20 Hz, 6H).

Sources & evidence

ORD record: ord-d083e6215e1b480482070fcd2054cad2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420830B2

Reaction notes

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