Triethylamine → HCID 86619876, compound

HRID 1958942Notes

Reaction equation

HRID 1958942 reaction equation
[CH2:1]([O:3][CH2:4][C@@H:5]([OH:8])[CH2:6][OH:7])[CH3:2].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH3:13][C:12]([Si:9]([CH3:11])([CH3:10])[O:7][CH2:6][C@H:5]([OH:8])[CH2:4][O:3][CH2:1][CH3:2])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 699975951575-06-5

Product 1

HCID 86619876HCID 86619876, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-3-ethoxy-1,2-propanediol (product from step (0.50 g) in DCM (30 mL) was added tert-butyldimethylsilyl chloride (0.88 g), triethylamine (0.43 mL) and 4-(dimethylamino)pyridine (31 mg) at 0° C. The solution was then warmed to ambient temperature and stirred for 16 h. The reaction mixture diluted with H2O and extracted with EtOAc. The organic layer was washed with brine and evaporated. Purification was by column chromatography on silica gel using EtOAc/isohexane (2:8) as eluent to give the subtitle compound as an oil. Yield: 0.69 g

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. customevaporated
  4. customPurification

Sources & evidence

ORD record
ord-af787bc0fdfd4d41b07721043d674138
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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