Tetrahydrofuran → (5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentan-1-ol

HRID 1756351Notes

Reaction equation

HRID 1756351 reaction equation
[Si]([O:18][CH:19]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])/[CH:20]=[CH:21]/[C:22]1[N:27]=[C:26]([CH:28]=[O:29])[CH:25]=[CH:24][CH:23]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].[NH4+].C(OCC)(=O)C.[O:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>>[OH:29][CH:28]([C:26]1[CH:25]=[CH:24][CH:23]=[C:22](/[CH:21]=[CH:20]/[CH:19]([OH:18])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[N:27]=1)[CH2:50][CH2:49][CH2:48][CH2:47][OH:46]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 883633866-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde

Product 1

HCID 19966481(5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentan-1-ol

Conditions

Temperature
-80 °C

Procedure

5.1 ml of a Grignard solution (produced from 385 mg of magnesium and 1.76 g of 4-chloro-1-tert-butyldimethylsilyloxybutane in tetrahydrofuran) is instilled at -80° C. in a solution of 370 mg of 6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde in 3 ml of tetrahydrofuran. After 2 hours of stirring at -80° C., the reaction mixture is poured into 10 ml of saturated ammonium chloride solution, shaken out with ethyl acetate, the organic phase is dried and concentrated by evaporation. The residue is dissolved in 10 ml of tetrahydrofuran, mixed with 2.47 g of tetrabutylammonium fluoride and stirred for 17 hours at room temperature. The reaction mixture is poured into 50 ml of diethyl ether, washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/0-30% ethyl acetate. 110 mg of the title compound is obtained as yellow oil.

Workup

  1. customthe organic phase is dried
  2. concentrationconcentrated by evaporation
  3. dissolutionThe residue is dissolved in 10 ml of tetrahydrofuran
  4. additionmixed with 2.47 g of tetrabutylammonium fluoride
  5. stirringstirred for 17 hours at room temperature
  6. additionThe reaction mixture is poured into 50 ml of diethyl ether
  7. washwashed with saturated common salt solution
  8. customdried on sodium sulfate
  9. concentrationconcentrated by evaporation
  10. customThe residue is chromatographed on silica gel with hexane/0-30% ethyl acetate

Sources & evidence

ORD record
ord-e93129dbbf9e4a9c94e933feb77c68cc
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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