Methanol → HCID 42622954, compound

HRID 1092446Notes

Reaction equation

HRID 1092446 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH3:46])=[CH:41][CH:40]=3)[CH:32]=2)[C@@H:11]([OH:47])[C@@H:10]1[CH2:48][O:49]CC1C=CC=CC=1)C1C=CC=CC=1.CO.ClC1C=CC=CC=1Cl.[H][H]>O1CCCC1.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:12]2[C@@H:11]([OH:47])[C@H:10]([CH2:48][OH:49])[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@H:13]2[OH:23])=[CH:32][C:33]=1[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][CH3:46])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 72391,2-DichlorobenzeneHCID 66588466HCID 66588466, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 42622954HCID 42622954, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)cyclohexanol (60 g, purity of 98%, 0.077 mol, 1 eq) in tetrahydrofuran:methanol (v/v=2:1) (600 mL) was added 1,2-dichlorobenzene (21.5 g, 16.54 mL, 0.82 mol, 2 eq), palladium on carbon (10%, 4.8 g) and was stirred for 4 h under an atmospheric pressure of hydrogen at room temperature (about 25° C.). The mixture was filtered and the filtrate was evaporated to dryness to give a yellow oil (80% pure).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto give a yellow oil (80% pure)

Sources & evidence

ORD record
ord-e5141200788a4a058e0a93fbb91dcc89
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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