Hexane → HCID 67304124, compound

HRID 1009861Notes

Reaction equation

HRID 1009861 reaction equation
[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][C:12]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)=[C:11]([CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH2:33]([O:40][C@@H:41]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@H:46]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C@@H:45]([CH2:64][O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[O:44][C:42]1=[O:43])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:33]([O:40][C@@H:41]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@H:46]([O:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C@@H:45]([CH2:64][O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[O:44][C:42]1([C:14]1[CH:13]=[C:12]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)[C:11]([CH3:21])=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:43])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 59141077HCID 59141077, compoundHCID 178418339Butyllithium

Product 1

HCID 67304124HCID 67304124, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a tetrahydrofuran solution (36 mL) of 2-[4-(benzyloxy)-5-bromo-2-methylphenyl]-1,3-dioxolane (5.82 g, 16.6 mmol) was added dropwise under nitrogen atmosphere at −78° C. a 2.67 M n-butyllithium solution in hexane (6.40 mL, 16.6 mmol), and the mixture was stirred for 30 minutes at the same temperature. Then a tetrahydrofuran solution (18 mL) of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone (8.16 g, 15.1 mmol) was added dropwise, and the mixture was stirred for 20 minutes at the same temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1) to obtain the title compound (10.7 g, 87%) as a yellow oily compound.

Workup

  1. stirringthe mixture was stirred for 20 minutes at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-2d033e0564e04a0298efe1f6f41bb242
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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