8-Chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene-6-carbaldehyde → 1-(8-Chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene-6-yl)-ethanol

HRID 2180535Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[C:4]([CH:17]=[O:18])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:13])([CH3:12])[CH:8]=[C:7]2[CH:14]([CH3:16])[CH3:15].[CH3:23][Mg]Cl>C1COCC1>[Cl:1][C:2]1[C:3]([O:19][CH:20]([CH3:22])[CH3:21])=[C:4]([CH:17]([OH:18])[CH3:23])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:12])([CH3:13])[CH:8]=[C:7]2[CH:14]([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 8-chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene-6-carbaldehyde, (Compound 135, 0.97 g, 3.0 mmol) in THF (15 mL) at was added methylmagnesium chloride (3M in THF, 1.6 mL, 4.8 mmol). After stirring at 0° C. for 30 min, the reaction was quenched with 1N HCl. The resulting mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound as a yellow foam.

Workup

customthe reaction was quenched with 1N HCl
additionThe resulting mixture was diluted with water
extractionextracted with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f47085a4623e4367a4d2b2ae88f94fd5
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

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