Triethylamine → HCID 23087566, compound

HRID 2278340Notes

Reaction equation

HRID 2278340 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][Si:32]([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 23087566HCID 23087566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-ol (1 g, 4.69 mmol), triethylamine (1.44 mL, 10.3 mmol) and dimethylaminopyridine (0.12 g, 0.94 mmol) in DCM (20 mL) at 0° C. was added TBSCl (1.56 g, 5.16 mmol). The reaction mixture was allowed to reach room temperature overnight, and then was quenched with a saturated solution of sodium bicarbonate (20 mL). The phases were separated and the aqueous layer was extracted twice with DCM (2×20 mL). The organics layers were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified on silica eluting with Et2O and pentane to afford the title compound.

Workup

  1. customwas quenched with a saturated solution of sodium bicarbonate (20 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted twice with DCM (2×20 mL)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified on silica eluting with Et2O and pentane

Sources & evidence

ORD record
ord-9db120b802c34f2eb1d6e98b6d2a2a0e
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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