2,6-Lutidine → HCID 70022958, compound

HRID 398312Notes

Reaction equation

HRID 398312 reaction equation
[Br:1][C:2]1[C:3]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:4][C:5]2[C:11]3([CH3:14])[CH:12]([OH:13])[C:7]([CH3:15])([CH2:8][CH2:9][CH2:10]3)[C:6]=2[CH:16]=1.N1C(C)=CC=CC=1C.O([Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:4][C:5]2[C:11]3([CH3:14])[CH:12]([O:13][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[C:7]([CH3:15])([CH2:8][CH2:9][CH2:10]3)[C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 23002523HCID 23002523, compound

Product 1

HCID 70022958HCID 70022958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

4.49 g of the thus-obtained (5RS,9SR,10RS)-2-bromo-3-heptyloxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene were placed in 12 ml of CH2Cl2 under argon and treated with 2.58 ml of 2,6-lutidine followed by 3.08 ml of t-butyldimethylsilyl triflate. The mixture was stirred at 35° C. overnight and then poured on to ice. The mixture was extracted with diethyl ether, washed with 1N HCl and water, dried over Na2SO4 and evaporated. Column filtration (SiO2/hexane) gave 5.39 g of (5RS,9SR,10RS)-2-bromo-10-t-butyldimethylsilyloxy-3-heptyloxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocycloheptene as a colourless oil.

Workup

  1. additionpoured on to ice
  2. extractionThe mixture was extracted with diethyl ether
  3. washwashed with 1N HCl and water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. filtrationColumn filtration (SiO2/hexane)

Sources & evidence

ORD record
ord-8af958b523c34ce98fef6d22e2317de0
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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