Acetone → HCID 131730695, compound

HRID 446649Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:12]=[C:11]([CH:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[O:14][SiH:15]([CH3:17])[CH3:16])[CH:10]=[C:9]([CH:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[O:23][SiH:24]([CH3:26])[CH3:25])[CH:8]=1.[CH3:31][C:32]([CH3:34])=[O:33].[NH4+].[Cl-]>CCCCCC.C1COCC1>[OH:33][C:32]([C:7]1[CH:12]=[C:11]([CH:13]([C:18]([CH3:20])([CH3:19])[CH3:21])[O:14][SiH:15]([CH3:17])[CH3:16])[CH:10]=[C:9]([CH:22]([C:27]([CH3:30])([CH3:28])[CH3:29])[O:23][SiH:24]([CH3:25])[CH3:26])[CH:8]=1)([CH3:34])[CH3:31]

Participants

Conditions

Temperature: -71 °C

Procedure

10.5 ml of n-BuLi as a 1.6M solution in hexane are added dropwise to 4.32 g of 1-bromo-3,5-bis[(tert-butyl)dimethylsilanyloxymethyl]benzene (G. T. Crisp and P. D. Turner, Tetrahedron, 2000, 56 (42), 8335) in solution in 150 ml of THF cooled to −71° C. After 1 h 30, 4.27 ml of acetone are added dropwise. The mixture is allowed to return to AT and then hydrolysed with a saturated aqueous NH4Cl solution. The aqueous phase is extracted with 100 ml of AcOEt, the combined organic phases are dried over MgSO4 and concentrated under RP, and the residue is purified by flash chromatography on silica (Biotage 65+M) using a gradient from 0 to 20% AcOEt in heptane. 2.48 g of 1-(1-hydroxy-1-methylethyl)-3,5-bis[(tert-butyl)dimethylsilanyloxymethyl]benzene are thus obtained.

Workup

extractionThe aqueous phase is extracted with 100 ml of AcOEt
dry with materialthe combined organic phases are dried over MgSO4
concentrationconcentrated under RP
customthe residue is purified by flash chromatography on silica (Biotage 65+M)

Sources & evidence

ORD record: ord-2c75fe631e4c4c39a0b66003a78e5d79
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481042B2

Reaction notes

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