Cesium fluoride → HCID 86729324, compound

HRID 1474634Notes

Reaction equation

HRID 1474634 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)O1.[F-].[Cs+].[C:19]([O:22][C@H:23]1[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@@H:28]([O:34][C:35](=[O:37])[CH3:36])[C@:27]2([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([CH2:46]Br)[CH:40]=3)[O:38][C@@:24]1([CH2:48][O:49][C:50](=[O:52])[CH3:51])[CH2:25][O:26]2)(=[O:21])[CH3:20]>O1CCOCC1.C(OC(=O)C)C>[C:19]([O:22][C@H:23]1[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@@H:28]([O:34][C:35](=[O:37])[CH3:36])[C@:27]2([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([CH2:46][C:9]4[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=4)[CH:40]=3)[O:38][C@@:24]1([CH2:48][O:49][C:50](=[O:52])[CH3:51])[CH2:25][O:26]2)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86729345HCID 86729345, compound2×

Product 1

HCID 86729324HCID 86729324, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (500 mg, 2.25 mmol), CsF (865.83 mg, 5.70 mmol) in Dioxane (9.5 mL), (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(3-(bromomethyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (1.07 g, 1.90 mmol, Intermediate 2) and Pd(PPh3) (173.3 mg, 0.15 mmol) were added under N2 atmosphere. The reaction mixture was heated to 110° C. for 1 h. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (20 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2:8 Acetone:hexane) to provide title compound (450 mg, 41.3%) as off-white solid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (20 mL) and brine (20 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 2:8 Acetone:hexane)

Sources & evidence

ORD record
ord-a605981170fc430cb2196ac836c412e9
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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