Triethylamine → HCID 86599785, compound

HRID 406808Notes

Reaction equation

HRID 406808 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(N(CC)CC)C.[S:16]1[C:20]([CH2:21][CH:22]([OH:25])[C:23]#[CH:24])=[CH:19][C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]1=2.[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.ClCCl>[S:16]1[C:20]([CH2:21][CH:22]([O:25][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6])[C:23]#[CH:24])=[CH:19][C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 21964441HCID 21964441, compound

Product 1

HCID 86599785HCID 86599785, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

DMAP (2.306 g, 18.9 mmol), TBSCl (11.502 g, 76.3 mmol) and triethylamine (5.25 mL, 37.7 mmol) were added to a solution of 9-4 (7.67 g, 37.9 mmol) in dichloromethane (120 mL). After 17 h, 150 mL of saturated NH4Cl solution was added and the layers were separated. The aqueous layer was extracted with dichloromethane (3×100 mL) and the combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (4% ethyl acetate/hexanes) gave 9-5 (8.38 g, 26.5 mmol, 70%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  3. dry with materialthe combined organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (4% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-15d5ec84f7c34c8a8c8973f967a49425
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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