Bromide ion → HCID 69049226, compound

HRID 1455697Notes

Reaction equation

HRID 1455697 reaction equation
[Br-].[CH3:2]C(C)([O-])C.[K+].[CH2:8]([O:10][C:11](=[O:32])[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:20][C:19]2=O)[CH3:9].O>O1CCCC1>[CH2:8]([O:10][C:11](=[O:32])[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:20][C:19]2=[CH2:2])[CH3:9]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 11858598HCID 11858598, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69049226HCID 69049226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

5.4 g (15.3 mmol) of methyltriphenylphosphate [sic] bromide are added to a suspension of 1.75 g (14.9 mmol) of potassium tert-butoxide in 20 ml of tetrahydrofuran. The reaction medium is stirred for 1 hour at 25° C. and then cooled to 0° C. A solution of 4.5 g (12.9 mmol) of ethyl4-(6-hexyl-3-oxoindan-5-yloxy)butyrate is added. The mixture is stirred for 16 hours at 25° C., poured into water and extracted with ether. The organic phase is dried (Na2SO4) and concentrated under reduced pressure (oil). Purification by flash chromatography (80/20 heptane/ethyl acetate) gives an orange oil (3.5 g; 79%).

Workup

  1. temperaturecooled to 0° C
  2. stirringThe mixture is stirred for 16 hours at 25° C.
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure (oil)
  6. customPurification by flash chromatography (80/20 heptane/ethyl acetate)
  7. customgives an orange oil (3.5 g; 79%)

Sources & evidence

ORD record
ord-132bbf1e362043e3bccaeb0898f4da83
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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