Triethylamine → HCID 22473228, compound

HRID 2183509Notes

Reaction equation

HRID 2183509 reaction equation
O.Cl.[OH:3][CH2:4][C:5]1[N:6]=[N:7][N:8]([CH3:10])[CH:9]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CCN(CC)CC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:11]([O:3][CH2:4][C:5]1[N:6]=[N:7][N:8]([CH3:10])[CH:9]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22321559HCID 22321559, compound

Product 1

HCID 22473228HCID 22473228, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxymethyl-1-methyl-1H-[1,2,3]triazole hydrochloride hydrate (WO-A-9850385) (7.0 g, 41.8 mmol), tert-butyldimethylsilyl chloride (6.3 g, 41.8 mmol), Et3N (11.6 ml, 83.6 mmol) and 4-(dimethylamino)pyridine (255 mg, 5 mol %) in CH2Cl2 (250 ml) was stirred at room temperature overnight under N2. Iso-hexanes (400 ml) were added and the resulting precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the mixture was purified by column chromatography on silica using 10-100% Et2O/iso-hexanes as eluent to yield the desired protected alcohol (8.90 g, 94%). 1H NMR (360 MHz, CDCl3) δ 7.35 (1H, s), 4.73 (2H, s), 3.98 (3H, s), 0.81(9H, s), 0.00 (6H, s).

Workup

  1. customthe resulting precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe mixture was purified by column chromatography on silica using 10-100% Et2O/iso-hexanes as eluent
  4. customto yield the

Sources & evidence

ORD record
ord-1ed906d7d7c04244ba53247eb4c31f48
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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