Triethylamine → HCID 86619876, compound

HRID 1175391Notes

Reaction equation

HRID 1175391 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 699975951575-06-52×

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 ii) (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-6e34f174b32e4efab783cd4df9b00fd1
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

Loading…