Ammonium Chloride → HCID 66765954, compound

HRID 556774Notes

Reaction equation

HRID 556774 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH:7]=[C:8]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C([Li])CCC.[CH2:24]([O:31][C@@H:32]1[C@@H:38]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:37]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:36]([CH2:55][O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[O:35][C:33]1=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:24]([O:31][C@@H:32]1[C@@H:38]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:37]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C@@H:36]([CH2:55][O:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[O:35][C:33]1([C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH:7]=[C:8]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1)[OH:34])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 66765807HCID 66765807, compoundHCID 178418339Butyllithium

Product 1

HCID 66765954HCID 66765954, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-3-(2-phenylethyl)benzo[b]-thiophene (0.94 g) in tetrahydrofuran (25 mL) was added n-butyllithium (2.44 mol/L n-hexane solution, 1.24 mL) at −78° C. under an argon atmosphere, and the mixture was stirred at the same temperature for 5 minutes. To the reaction mixture was added a solution of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone (0.80 g) in tetrahydrofuran (4 mL), and the mixture was warmed to 0° C. and stirred for 30 minutes. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/1) to give the title compound (1.1 g).

Workup

  1. stirringstirred for 30 minutes
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/1)

Sources & evidence

ORD record
ord-1517d4ad399f434b9538421252666041
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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