Triethylamine → (1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 407840

Reaction equation

HRID 407840 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:13]2[CH:8]([CH:9]3[O:14][CH:12]2[CH2:11][CH2:10]3)[C:7](=[O:15])[CH:6]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:6]1[C:7](=[O:15])[CH:8]2[CH:13]([C:5]=1[O:4][CH3:3])[CH:12]1[O:14][CH:9]2[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Product 1

HCID 67283643(1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.14 ml, 2.8 mmol) in dichloromethane (5 ml) is added dropwise to a solution of the enol ether (0.48 g, 2.6 mmol) prepared in step 1 in dichloromethane (40 ml) at 0° C. and the reaction mixture is stirred for 1 hour. Triethylamine (0.64 ml, 4.6 mmol) is then added and the reaction mixture is allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture is washed with 2M aqueous hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one.

Workup

  1. stirringstirred for 3 hours
  2. washThe reaction mixture is washed with 2M aqueous hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-13fc2705a1474372abe61736e60ceacd
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Linked notes

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