tert-Butyldimethylsilyl chloride → HCID 67257131, compound

HRID 2371033Notes

Reaction equation

HRID 2371033 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:7][CH2:8][OH:9])[S:5][CH:6]=1.C(N(C(C)C)CC)(C)C.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[C:20]([Si:23]([CH3:25])([CH3:24])[O:9][CH2:8][CH2:7][C:4]1[S:5][CH:6]=[C:2]([CH3:1])[CH:3]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 21541858HCID 21541858, compound

Product 1

HCID 67257131HCID 67257131, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-methylthiophen-2-yl)ethanol (3.0 g, 21.1 mmol) and diisopropylethylamine (4.1 g, 31.7 mmol) in dry DCM (50 mL) at 0° C. was added TBSCl (4.8 g, 32.0 mmol) in dry DCM (20 mL) dropwise and the mixture was then warmed to room temperature gradually. After the alcohol was consumed completely, water (10 mL) was added. The resulting mixture was extracted with DCM (3×100 mL), washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (5.1 g, 94%).

Workup

  1. customAfter the alcohol was consumed completely
  2. additionwater (10 mL) was added
  3. extractionThe resulting mixture was extracted with DCM (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-61146caf60824e17bd4146bd2535860e
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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