Triethylamine → HCID 86619876, compound

HRID 1024886Notes

Reaction equation

HRID 1024886 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-281abc8a955144249d33631b7683c90a
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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