Aluminum(III) Chloride → HCID 67074671, compound

HRID 1944086Notes

Reaction equation

HRID 1944086 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:11][C@H:10]1[C:52]1[CH:57]=[CH:56][C:55]([Cl:58])=[C:54]([CH2:59][C:60]2[CH:65]=[CH:64][C:63]([O:66][CH2:67][CH3:68])=[CH:62][CH:61]=2)[CH:53]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.C(OCC)C.O.C([O-])(O)=O.[Na+]>[CH2:24]([O:23][C@H:13]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:10]([C:52]2[CH:57]=[CH:56][C:55]([Cl:58])=[C:54]([CH2:59][C:60]3[CH:61]=[CH:62][C:63]([O:66][CH2:67][CH3:68])=[CH:64][CH:65]=3)[CH:53]=2)[O:11][C@@H:12]1[CH2:31][OH:32])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86668481HCID 86668481, compound

Product 1

HCID 67074671HCID 67074671, compoundYield 50.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran (12.2 g, 17.9 mmole) in dry DCM (50 mL), AlCl3 (2.8 gm, 21.5 mmole) in diethyl ether was added at 0° C. and stirred at room temperature for 2 hours. The reaction mixture was diluted with water (500 mL) and saturated aqueous NaHCO3 (50 mL), extracted with DCM (2×250 mL). The crude product obtained after the removal of solvent was purified using silica gel column chromatography (10% ethyl acetate in hexane) to furnish 6.1 g of {(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydro-pyran-2-yl}-methanol.

Workup

  1. extractionextracted with DCM (2×250 mL)
  2. customThe crude product obtained
  3. customafter the removal of solvent
  4. customwas purified

Sources & evidence

ORD record
ord-27574aa1d1b34df5a036666027a4113e
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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