Methyl iodide → HCID 13393812, compound

HRID 978780Notes

Reaction equation

HRID 978780 reaction equation
[Mg].[CH3:2]I.[Cl:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH:21]=[O:22].[Cl-].[NH4+]>O.O1CCCC1.C(OCC)C>[Cl:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][CH:7]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6]=1[CH:21]([OH:22])[CH3:2]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 13393783HCID 13393783, compound

Product 1

HCID 13393812HCID 13393812, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.88 g magnesium is allowed to react with 16.82 g methyl iodide in 80 ml refluxing dry diethylether. After disappearance of magnesium, one adds a solution of 21.4 g 4-chloro-3-formyl-flav-3-ene in 100 ml of a mixture of diethylether and tetrahydrofuran. After cooling to 0° C., a solution of 12.68 g ammonium chloride in 160 ml water is added. The two phases are separated and the aqueous solution is extracted with 50 ml diethyl ether. The combined organic phases are washed with 50 ml water, dried over magnesium sulfate and evaporated. The crude solid is crystallized in hexane. A racemate of one diastereomer of 4-chloro-3-(α-hydroxyethyl)-flav-3-ene is obtained as yellow crystals; m.p. 111°-113° C.

Workup

  1. customThe two phases are separated
  2. extractionthe aqueous solution is extracted with 50 ml diethyl ether
  3. washThe combined organic phases are washed with 50 ml water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude solid is crystallized in hexane

Sources & evidence

ORD record
ord-c82c1b94997d48b2b9a5bb37e6e30adf
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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