Hexane → HCID 53703705, compound

HRID 962357Notes

Reaction equation

HRID 962357 reaction equation
[Br-].[CH:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.CCCCCC.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[N:59]=[CH:58][C:57]([CH:60]=O)=[CH:56][N:55]=2)=[CH:50][CH:49]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>COC(C)(C)C.O1CCCC1>[CH:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:60][C:57]2[CH:58]=[N:59][C:54]([C:51]3[CH:52]=[CH:53][C:48]([O:47][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:49][CH:50]=3)=[N:55][CH:56]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 8058HexaneHCID 19083469HCID 19083469, compoundHCID 19083563HCID 19083563, compound

Product 1

HCID 53703705HCID 53703705, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension of 3.7 g of (8-cyclopentyl-octyl)-triphenylphosphonium bromide (prepared by heating 3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product from the cooled reaction mixture by addition of hexane) in 20 ml of tert.-butyl methyl ether is treated with 0.8 g of potassium tert.-butylate and the yellow suspension is stirred at room temperature for 45 minutes. Then, a solution of 1.64 g of 2-(4-heptyloxy-phenyl)-pyrimidine-5-carboxaldehyde in 10 ml of tetrahydrofuran is added dropwise at 0° to 5° C. The reaction mixture is stirred at 0° C. for a further 2 hours and then triturated with 10 ml of saturated sodium hydrogen carbonate solution. The phases are separated and the organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue is partitioned between methanol/water (vol.) 4:1 and hexane and the methanol phase is separated. The hexane phase is washed with methanol/water 4:1 and the filtrate is concentrated. The crude 5-(9-cyclopentyl-non-1-enyl)-2-(4-heptyloxy-phenyl)-pyrimidine obtained is purified by chromatography on 10 g of silica gel with hexane/ethyl acetate 19:1 (v/v).

Workup

  1. customprepared
  2. temperatureby heating
  3. custom3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product
  4. customfrom the cooled reaction mixture
  5. stirringThe reaction mixture is stirred at 0° C. for a further 2 hours
  6. customtriturated with 10 ml of saturated sodium hydrogen carbonate solution
  7. customThe phases are separated
  8. washthe organic phase is washed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is partitioned between methanol/water (vol.) 4:1 and hexane
  13. customthe methanol phase is separated
  14. washThe hexane phase is washed with methanol/water 4:1
  15. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-1cf214474bb94f7ea944c10755923420
Source dataset
uspto-grants-1998_06
Patent number
US05759443

Reaction notes

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