Ammonium Chloride → HCID 23150776, compound

HRID 908909Notes

Reaction equation

HRID 908909 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[O:5]1[C:10]2[CH:11]=[CH:12][C:13]([CH:15]=[O:16])=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1.[Cl-].[NH4+]>O1CCCC1>[OH:16][CH:15]([C:13]1[CH:12]=[CH:11][C:10]2[O:5][CH2:6][CH2:7][O:8][C:9]=2[CH:14]=1)[CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 23150776HCID 23150776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of vinylmagnesiumbromide in tetrahydrofurane (29 mL 1M) maintained at a temperature below 4° C. is added portionwise 2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (4.32 g). The mixture is further stirred at a temperature close to 0° C. for 1.75 h and hydrolized by adding an aqueous solution of ammonium chloride (36.5 mL 1M). The mixture is extracted with diethyl oxide. The organic layers are pooled, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography over silica gel, with heptane/ethyl acetate 1/1 as eluant, affords 1.12 g of 2,3-dihydro-6-(1-hydroxyallyl)benzo[1,4]dioxine as a yellow oil used without further purification.

Workup

  1. customclose to 0° C. for 1.75 h
  2. extractionThe mixture is extracted with diethyl oxide
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography over silica gel

Sources & evidence

ORD record
ord-e828f9be03a3432e8437c54622824ef2
Source dataset
uspto-grants-2011_09
Patent number
US08017646B2

Reaction notes

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