tert-Butyldimethylsilyl chloride → HCID 58775972, compound

HRID 2354262Notes

Reaction equation

[CH2:1]([C:3]([C:14]1[CH:27]=[CH:26][C:17]([O:18][CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:16]([CH3:28])[CH:15]=1)([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:29][C:30]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])[CH3:31]>>[C:30]([Si:33]([CH3:35])([CH3:34])[O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]([C:14]2[CH:27]=[CH:26][C:17]([O:18][CH2:19][C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])=[C:16]([CH3:28])[CH:15]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][C:8]=1[CH3:13])([CH3:32])([CH3:31])[CH3:29]

Participants

Reactant 2

HCID 28928tert-Butyldimethylsilyl chloride

HCID 20647490HCID 20647490, compound

Product 1

HCID 58775972HCID 58775972, compoundYield 90.2%

Procedure

Using a procedure analogous to Example 13A, 1-{(4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (Example 1B) (4.91 g, 12.83 mmol) and TBSCl (1.93 g, 12.83 mmol) give the title compound (5.74 g, 11.57 mmol, 90%). 1H NMR (CDCl3), δ 0.21 (s, 6H), 0.60 (t, J=7.5 Hz, 6H), 1.01(s, 9H), 1.26 (s, 9H), 2.01 (q, J=7.5 Hz, 4H), 2.16 (s, 3H), 2.24 (s, 3H), 4.83 (s, 2H), 6.50 (d, J=8.4 Hz, 1H), 6.63 (d, J=8.4 Hz, 1H), 6.82 (dd, J=8.4, 2.3 Hz, 1H), 6.87-6.93 (m, 3H). LC/MS (m/z): calcd for C31H52NO3Si (M+NH4)+: 514.8; found: 514.5.

Sources & evidence

ORD record: ord-f836d5520bf942da91bb63f4fd052cf1
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750184B2

Reaction notes

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