Nitrogen → 2-[1-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole

HRID 2065058Notes

Reaction equation

HRID 2065058 reaction equation
N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][OH:17])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].CCN(CC)CC.[S:27]([Cl:31])([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][Cl:31])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][O:17][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:14][N:15]=1)[CH3:10])([CH3:5])([CH3:4])[CH3:6]

Participants

8

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66821254HCID 66821254, compound

Product 2

HCID 668212212-[1-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazoleHCID 87207847Methanesulfonic acid 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of {2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-yl}-methanol (455 mg, 1.77 mmol) in dry CH2Cl2 (4.5 mL) was treated at 0° C. with Et3N (0.32 mL, 2.30 mmol) followed by DMAP (22 mg, 0.18 mmol) and Ms-Cl (0.17 mL, 2.12 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give in a 2:1 ratio the title compound (LC-MS-conditions 02: tR=1.13 min, [M+H]+=276.06) along with methanesulfonic acid 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl ester (LC-MS-conditions 02: tR=1.07 min, [M+H]+=336.45) as a pale yellow oil.

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c1076391995e48d5b2eb7c8dea20123e
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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