Bromine → HCID 20481706, compound

HRID 1648735Notes

Reaction equation

HRID 1648735 reaction equation
[C:1]([CH:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].[H-].[Na+].[Br:26]Br>O1CCCC1.ClCCl>[C:1]([C:4]([Br:26])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24408BromineHCID 24758Sodium hydrideHCID 20481701HCID 20481701, compound

Product 1

HCID 20481706HCID 20481706, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-acetyl-9-tetrahydropyranyloxy-nonanoate (20 g) in dry tetrahydrofuran (100 ml) was added dropwise to a stirred suspension of sodium hydride (2.01 g of 80% oil dispersion) in dry tetrahydrofuran (50 ml), under nitrogen. The mixture was warmed to reflux for 10 minutes. The clear solution was allowed to cool to room temperature then a solution of bromine (3.15 ml) in dry dichloromethane (50 mls) was added rapidly. After stirring for 30 minutes, during which time a yellow precipitate was formed, the mixture was partitioned between water and ether. The ether solution was washed with brine, dried and evaporated in vacuo at low temperature (<30° C.). The ethyl 2-acetyl-2-bromo-9-tetrahydropyranyloxy-nonanoate was obtained as a dark yellow oil (27.1 g.) which still contained a small amount of solvent.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 10 minutes
  3. customwas formed
  4. customthe mixture was partitioned between water and ether
  5. washThe ether solution was washed with brine
  6. customdried
  7. customevaporated in vacuo at low temperature (<30° C.)

Sources & evidence

ORD record
ord-fb930093e3564552b1be2d1ceb84bfdf
Source dataset
uspto-grants-1983_11
Patent number
US04413002

Reaction notes

Loading…