1,2-Dichlorobenzene → HCID 86685106, compound

HRID 1912987Notes

Reaction equation

HRID 1912987 reaction equation
C([O:8][C@H:9]1[C@H:15]([O:16]CC2C=CC=CC=2)[C@@H:14]([O:24]CC2C=CC=CC=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][O:50][CH:51]5[CH2:53][CH2:52]5)=[CH:43][CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH2:54][OH:55])[CH2:11][O:12]2)C1C=CC=CC=1.C1COCC1.ClC1C=CC=CC=1Cl>[Pd].CO>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@@:13]23[O:32][C@@:10]([CH2:54][OH:55])([CH2:11][O:12]2)[C@@H:9]([OH:8])[C@H:15]([OH:16])[C@H:14]3[OH:24])=[CH:34][C:35]=1[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][O:50][CH:51]2[CH2:53][CH2:52]2)=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 8028TetrahydrofuranHCID 86685105HCID 86685105, compound

Product 1

HCID 86685106HCID 86685106, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[(1S,2S,3S,4R,55)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 1g (220.3 mg, 0.29 mmol) was dissolved in 10 mL mixed solution (THF and MeOH, v:v=1:1), followed by addition of 1,2-dichlorobenzene (0.34 mL, 3 mmol) and Palladium/carbon (90 mg, 10%). The mixture was exchanged with H2 three times and stirred for 3 hours, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (1S,2S,3S,4R,5S)-5-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 1 (140 mg, white solid), yield: 100%. MS m/z (ESI): 510.2 [M+18]. 1H NMR (400 MHz, CD3OD): δ 7.45 (d, 1H), 7.36 (m, 2H), 7.10 (d, 2H), 6.82 (m, 2H), 4.14 (d, 1H), 4.05 (m, 4H), 3.83 (m, 3H), 3.78 (m, 1H), 3.66 (m, 2H), 3.57 (m, 2H), 3.40 (m, 1H), 0.56 (m, 2H), 0.48 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel chromatography with elution system

Sources & evidence

ORD record
ord-7ec9df6f67a347dbb3a8503c13c209bf
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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