tert-Butyldimethylsilyl chloride → HCID 86678084, compound

HRID 2274708Notes

Reaction equation

HRID 2274708 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>N1C=CC=CC=1.C1COCC1.[N+]([O-])([O-])=O.[Ag+]>[Si:29]([O:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][C:4]([O:6][CH3:7])=[O:5])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86678082HCID 86678082, compound

Product 1

HCID 86678084HCID 86678084, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

The alcohol (11Z,14Z)-methyl 3-hydroxyicosa-11,14-dienoate (3) (1.40 g, 4.14 mmol) in pyridine:THF (2:1, 30 mL) was treated with silver nitrate (913 mg, 5.40 mmol), t-butylchlorodimethyl silane (814 mg, 5.40 mmol) and stirred (60 min) The mixture was filtered through Celite and the filter cake rinsed with pyridine. The filtrate was concentrated and the residue was taken-up in CH2Cl2, washed with HCl (5%, aq.) and brine, dried, filtered and concentrated. The crude material was subjected to chromatography to yield (11Z,14Z)-methyl 3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienoate (4) (1.70 g, 91%) as a clear colorless oil. Rf 0.8 (10% EtOAc-hexanes), FW 452.79, C27H52O3Si.

Workup

  1. filtrationwas filtered through Celite
  2. washthe filter cake rinsed with pyridine
  3. concentrationThe filtrate was concentrated
  4. washwashed with HCl (5%, aq.) and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2d07e8ef6e44258b1e13e346456571d
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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