Hexane → HCID 59141072, compound

HRID 1641525Notes

Reaction equation

HRID 1641525 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.CCCCCC.[CH2:18]([O:25][C@@H:26]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[S:29][C:27]1([C:58]1[CH:63]=[C:62]([CH:64]=[O:65])[C:61]([CH3:66])=[CH:60][C:59]=1[O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[OH:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>O1CCCC1.C([Li])CCC>[CH2:18]([O:25][C@@H:26]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[S:29][C@:27]1([C:58]1[CH:63]=[C:62]([CH:64]([OH:65])[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=2)[C:61]([CH3:66])=[CH:60][C:59]=1[O:67][CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)[OH:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 104659191-Bromo-4-(methoxymethoxy)benzeneHCID 59141091HCID 59141091, compound

Product 1

HCID 59141072HCID 59141072, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-4-(methoxymethoxy)benzene (1.55 g, 7.13 mmol) in tetrahydrofuran (7.5 mL), 2.67 M n-butyllithium in hexane (2.58 mL, 6.9 mmol) was added dropwise at −60° C. under a nitrogen atmosphere. Then, a solution of 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-formyl-4-methylphenyl]-5-thio-D-glucopyranose (1.80 g, 2.30 mmol) in tetrahydrofuran (10 mL) was added dropwise and stirred at −78° C. for 10 minutes. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1) to give the titled compound (1.2 g, 57%) as a yellow amorphous substance.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtering off the desiccant
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1)

Sources & evidence

ORD record
ord-39048039b8b24092afdf1fe4cd95142f
Source dataset
uspto-grants-2012_02
Patent number
US08115017B2

Reaction notes

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