Sulfuric Acid → HCID 131734656, compound

HRID 1771446Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C@@H:5]([CH3:17])[O:6][CH:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH-].[K+].[OH:20]S(O)(=O)=O>O1CCOCC1.O.CCO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:20][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C@@H:5]([CH3:17])[O:6][CH:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3R)-ethyl 5bromo-3-methylisochroman-1-carboxylate (2.0 g, 5.95 mmol) in dioxane (50 ml) and water (10 ml) was added KOH (1.37 g, 35.7 mmol), tetramethyl dit-butyl XPhos (0.28 g, 0.06 mmol) and Pd2(dba)3 (0.06 g, 0.06 mmol) at room temperature. Then, reaction mixture was degassed three times with N2 and stirred at 100° C. for 16 h. The reaction mixture was quenched with MeOH and concentrated under reduced pressure to afford crude compound. The crude was dissolved in EtOH (80 ml) added H2SO4 (1.0 ml) then stirred at 80° C. for 5 h. The solvent was removed by evaporation to get the crude compound. The title compound was purified by separation methods A and E. (Yield 100 mg).

Workup

customThen, reaction mixture
customwas degassed three times with N2
customThe reaction mixture was quenched with MeOH
concentrationconcentrated under reduced pressure
customto afford crude compound
stirringthen stirred at 80° C. for 5 h
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-b564badd37f24870b59340c04e7db103
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249127B2

Reaction notes

Loading…