Sodium Hydroxide → HCID 66878306, compound

HRID 39007Notes

Reaction equation

HRID 39007 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:14])[C:5]2[O:10][CH2:9][C@H:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=1.[CH3:15][S:16]([O-:18])=[O:17].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O.[Cu]I>[F:14][C:4]1[C:5]2[O:10][CH2:9][C@H:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=[C:2]([S:16]([CH3:15])(=[O:18])=[O:17])[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 66879256HCID 66879256, compound

Product 1

HCID 66878306HCID 66878306, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Preparation according to Preparation 21 using [(2S)-7-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.35 g, 8.9 mmol), sodium methanesulfinate (85%) (1.29 g, 107 mmol), CuI (0.34 g, 1.8 mmol), L-proline (0.41 g, 3.6 mmol) and NaOH (0.071 g, 1.8 mmol) in DMSO (6 ml). Yield 0.98 g. MS m/z (rel. intensity, 70 eV) 262 (M+, bp), 231 (35), 183 (22), 152 (23), 57 (30).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-cbaa0231d4e44f46bb624d453c3133ab
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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