Triethylamine → HCID 15777972, compound

HRID 981829Notes

Reaction equation

HRID 981829 reaction equation
[CH2:1]1[C:10](=[O:11])[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:19]([O:11][C:10]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:9]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 682662-Tetralone

Product 1

HCID 15777972HCID 15777972, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Charge an oven dried, nitrogen flushed 125-mL round bottomed flask equipped with a stirring bar with β-tetralone (4.977 grams, 0.0340 moles), triethylamine (6.970 grams, 0.0689 moles), 4-dimethylamino pyridine (0.217 grams, 0.0018 moles), t-butyldimethylsilyl chloride (10.701 grams, 0.0709 moles) and 40 mL methylene chloride. Stir for 72 hours, filter, wash the filtrate with 1×5 mL saturated sodium bicarbonate solution, 1×5 mL water, dry over magnesium sulfate, concentrate using a Buchi rotavapor and distill (142°-145° C., 1 Torr) to obtain the named compound

Workup

  1. additionCharge an oven
  2. customdried
  3. customnitrogen flushed 125-mL round bottomed flask
  4. filtrationfilter
  5. washwash the filtrate with 1×5 mL saturated sodium bicarbonate solution, 1×5 mL water
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate
  8. distillationdistill (142°-145° C., 1 Torr)
  9. customto obtain the named compound

Sources & evidence

ORD record
ord-b54b27b8d3164bdfadeae673830f6fda
Source dataset
uspto-grants-1991_02
Patent number
US04992591

Reaction notes

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