Hexane → HCID 22733408, compound

HRID 2084567Notes

Reaction equation

HRID 2084567 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH3:22])=[N:19][C:18]=2[CH:23]=1.[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[C:25]1=[O:34])[CH2:31]2>C1COCC1.C(OCC)(=O)C.C(O)(=O)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH2:22][C:25]3([OH:34])[CH:26]4[CH2:32][CH:30]5[CH2:29][CH:28]([CH2:33][CH:24]3[CH2:31]5)[CH2:27]4)=[N:19][C:18]=2[CH:23]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 64151Adamantanone2×HCID 76252Benzothiazole, 5-methoxy-2-methyl-2×HCID 178418339Butyllithium

Product 1

HCID 22733408HCID 22733408, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 mL of a 1.6 M n-butyllithium solution is hexane are added dropwise to a solution of 358 mg of 5-methoxy-2-methylbenzothiazole (formula VIII) in 5 ml of dry THF, cooled to about −78°and the mixture obtained is stirred for about one hour. Solid 2-adamantanone (formula VI) is added and the mixture is kept at −78° for about one hour. The mixture is allowed to warm to room temperature and 400 μl of acetic acid are added. The resultant mixture is diluted with 600 ml of ethyl acetate and extracted with saturated NaH2PO4 solution. The solvent of the organic phase is evaporated off and the residue obtained is subjected to chromatography. The title compound is obtained (m.p. 140-142°).

Workup

  1. temperaturecooled to about −78°and the mixture
  2. customobtained
  3. waitthe mixture is kept at −78° for about one hour
  4. extractionextracted with saturated NaH2PO4 solution
  5. customThe solvent of the organic phase is evaporated off
  6. customthe residue obtained

Sources & evidence

ORD record
ord-dbbbec843dc34c318bf4547a3c6c7e74
Source dataset
uspto-grants-2004_04
Patent number
US06716865B1

Reaction notes

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