Dichloromethane → HCID 86729341, compound

HRID 1474597Notes

Reaction equation

HRID 1474597 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:31][CH3:32])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C@H:10]([O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C@H:9]2[O:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:4][C:3]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)Cl.C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:31][CH3:32])[O:13][C@H:12]([CH:14]=[O:15])[C@@H:11]([O:16][Si:17]([CH3:20])([CH3:18])[CH3:19])[C@H:10]([O:21][Si:22]([CH3:23])([CH3:24])[CH3:25])[C@H:9]2[O:26][Si:27]([CH3:28])([CH3:29])[CH3:30])=[CH:4][C:3]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 86729342HCID 86729342, compound

Product 1

HCID 86729341HCID 86729341, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of ((2R,3R,4S,5R,6S)-6-(4-chloro-3-(phenoxymethyl)phenyl)-6-methoxy-3,4, 5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol (23.0 g, 36.7 mmol) in DMSO (250 mL) was added DCM (20 mL) to make a clear solution. The solution was cooled to 0° C. followed by addition of triethyl amine (122.4 ml, 881.0 mmol) and sulphur trioxide pyridine complex (87.5 g, 550.6 mmol). The reaction mixture was stirred at 0 to 10° C. for 3 h under nitrogen atmosphere. After completion of the reaction as confirmed by TLC, the crude compound was extracted with diethyl ether (1 L). The organic layer was separated, washed with water (2×500 mL), dried over Na2SO4, concentrated in vacuo to afford crude title compound (22.9 g, 100%) as a viscous oil which was used for next step without any purification.

Workup

  1. customAfter completion of the reaction
  2. extractionthe crude compound was extracted with diethyl ether (1 L)
  3. customThe organic layer was separated
  4. washwashed with water (2×500 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ef526120903485ebcac8d1003d682b2
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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