Triethylamine → HCID 618241, compound

HRID 2306187Notes

Reaction equation

HRID 2306187 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:27]([O:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 618241HCID 618241, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole, as described in Example 1, Step A, (1.97 g, 5.72 mmol) and 4-(dimethylamino) pyridine (280 mg, 2.29 mmol) were stirred in CH2Cl2 (15 mL) and tert-butyldimethylsilyl chloride (905 mg, 6.01 mmol) was added. After 1 min, triethylamine (0.88 mL, 6.31 mmol) was added dropwise over 3 min. The reaction mixture was stirred for 45 min, then CH2Cl2 (150 mL) was added and the solution was washed with 0.1 N HCl (50 mL). The organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane—30% EtOAc, to yield the titled product as a white solid.

Workup

  1. washthe solution was washed with 0.1 N HCl (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with hexane—30% EtOAc

Sources & evidence

ORD record
ord-ad73779686a947a583a0d1a45dd658af
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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