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Sodium Chloride → HCID 131723900, compound

HRID 1374578
Notes
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Reaction equation

HRID 1374578 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[OH:22])([CH3:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[Br:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].[Cl-].[Na+]>O1CCCC1.O.CCOCC>[C:4]([Si:1]([CH3:2])([CH3:3])[O:8][CH2:9][CH2:10][C:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[OH:22])([CH3:12])[CH3:13])([CH3:7])([CH3:6])[CH3:5].[Br:25][CH2:26][CH2:27][CH2:28][C:29]([O-:30])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 702254-Bromobutyryl chlorideHCID 152992832-(4-((tert-Butyldimethylsilyl)oxy)-2-methylbutan-2-yl)-3,5-dimethylphenol

Product 1

HCID 131723900HCID 131723900, compound

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To 3.22 g of 2-{3-(tert-butyldimethylsilyloxy)-1,1-dimethylpropyl}-3,5-dimethyl-phenol in solution in 60 cm3 of tetrahydrofuran, there are added, at 20° C. under an argon atmosphere and in small portions, 0.32 g of sodium hydride (at 75% in mineral oil), and then 15 minutes later 1.16 cm3 of 4-bromobutyryl chloride. After stirring for 40 minutes, 100 cm3 of ether, 10 cm3 of distilled water and 10 cm3 of a saturated aqueous sodium chloride solution are added. After stirring, the organic phase is decanted off, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is filtered on 75 g of silica (particle size 0.063–0.2 mm), eluting successively with cyclohexane and then with a cyclohexane/ethyl acetate mixture (90/10 by volume). 2 g of 2-{3-(tert-butyldimethyl-silyloxy)-1,1-dimethylpropyl}-3,5-dimethylphenol 4-bromobutyrate are thus obtained in the form of a colorless oil.

Workup

  1. stirringAfter stirring
  2. customthe organic phase is decanted off
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customto give a residue which
  7. filtrationis filtered on 75 g of silica (particle size 0.063–0.2 mm)
  8. washeluting successively with cyclohexane

Sources & evidence

ORD record
ord-c88f4c441c0946a3af1123beeed42720
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166594B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes