Triethylamine → HCID 11157507, compound

HRID 2087025Notes

Reaction equation

HRID 2087025 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[C:5]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:4][C:3]=1[OH:25].[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[Br:1][C:2]1[C:3]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:4][C:5]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])=[C:6]([O:9][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:11])[CH3:12])[C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11167257HCID 11167257, compound

Product 1

HCID 11157507HCID 11157507, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.042 g (0.090 mmol) of 17, 0.016 g (0.11 mmol) of t-butyldimethylsilyl chloride, and 0.003 g (0.010 mmol) of DMAP in 2 mL of dichloromethane under argon at 25° C. was added 0.05 mL (0.260 mmol) of triethylamine. The reaction mixture was stirred for 3 h, diluted with 30 mL of water, and extracted three times with diethyl ether (30 mL each). The combined ether extracts were with 30 mL of brine, dried (MgSO4), and concentrated to give 0.051 g (99% yield) of 4.

Workup

  1. extractionextracted three times with diethyl ether (30 mL each)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-952ad99d6b1244b48c7835c817a2dfa7
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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