Triethylamine → HCID 58951491, compound

HRID 1445749Notes

Reaction equation

HRID 1445749 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:23])=[C:18]([CH2:20][CH2:21][OH:22])[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]([Si:35](Cl)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH3:34])([CH3:33])[CH3:32]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:23])=[C:18]([CH2:20][CH2:21][O:22][Si:35]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 22261180HCID 22261180, compound

Product 1

HCID 58951491HCID 58951491, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-[2-(4-Benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethanol [CAS 403611-91-6] (4.04 g, 13.0 mmol), triethylamine (3.6 mL, 25 mmol, and DMAP (0.16 g, 1.3 mmol) in CH2Cl2 (80 mL) at 0° C. is added a solution of tert-butylchlorodiphenylsilane (3.95 g, 14.4 mmol) in CH2Cl2 (10 mL) drop wise. The mixture is warmed to room temperature and stirred for 6 h. The mixture is washed with 0.5 N HCl (80 mL), and the organic phase is dried (MgSO4). After the solvent is removed in vacuo, the residue is purified by flash chromatography (elute 2:1 hexanes:EtOAc) to yield 7.09 g of the title compound as a white solid. MS (ES+) 548

Workup

  1. washThe mixture is washed with 0.5 N HCl (80 mL)
  2. dry with materialthe organic phase is dried (MgSO4)
  3. customAfter the solvent is removed in vacuo
  4. customthe residue is purified by flash chromatography (elute 2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-8ab778f07af943c380232f7d57eb0c4b
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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