Triethylamine → HCID 86759530, compound

HRID 1006745Notes

Reaction equation

HRID 1006745 reaction equation
[CH2:1](N(CC)CC)C.[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:15]([Si:19](Cl)([CH3:21])[CH3:20])(C)(C)C>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][Si:19]([CH3:21])([CH3:1])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 789155-Chloro-1-pentanol

Product 1

HCID 86759530HCID 86759530, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-10 °C

Procedure

13.8 ml of triethylamine and then 200 mg of 4-dimethyl amino-pyridine were added under a nitrogen atmosphere to a solution of 10.2 g of 5-chloropentanol in 80 ml of methylene chloride. The mixture was cooled down to −10° C. and 13.75 g of tertbutyl chloro dimethyl-silane were added. The mixture was stirred for 15 minutes at −10° C. then left to reheat to ambient temperature and diluted with a saturated solution of sodium bicarbonate. The oily crude derivative was separated out and chromatographed on silica (eluant:cyclohexane-ethyl acetate 95-5) to obtain 18 g of the expected product.

Workup

  1. waitthen left
  2. customto reheat to ambient temperature
  3. customThe oily crude derivative was separated out
  4. customchromatographed on silica (eluant:cyclohexane-ethyl acetate 95-5)

Sources & evidence

ORD record
ord-37fbde3be31646af8e7abce7914b55f0
Source dataset
uspto-grants-2004_09
Patent number
US06790971B1

Reaction notes

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