Diethyl Ether → 2-[1-Hydroxy-1-[3-methoxy-5-(naphth-2-ylmethoxy)phenyl]propyl]thiazole

HRID 1534601Notes

Reaction equation

HRID 1534601 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:11]=[C:10]([O:26][CH3:27])[CH:9]=1)=[O:7].[CH2:28](OCC)[CH3:29].C([Mg]I)C.[Cl-].[NH4+]>O1CCCC1>[OH:7][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:11]=[C:10]([O:26][CH3:27])[CH:9]=1)[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 197730783-Methoxy-5-(naphth-2-ylmethoxy)phenyl 2-thiazolyl ketoneHCID 178461634HCID 178461634, compound

Product 1

HCID 197730412-[1-Hydroxy-1-[3-methoxy-5-(naphth-2-ylmethoxy)phenyl]propyl]thiazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ketone so obtained (1.2 g) in tetrahydrofuran (20 ml) was added to a diethyl ether solution of ethylmagnesium iodide [prepared from iodoethane (0.6 ml) and magnesium turnings (0.154 g) under diethyl ether (10 ml)] and the mixture was heated to reflux for 15 minutes. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3×15 ml). The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with methylene chloride/ethyl acetate (17/3 v/v) to give 2-[1-hydroxy-1-[3-methoxy-5-(naphth-2-ylmethoxy) phenyl]propyl]thiazole (0.72 g, 55%), m.p. 105° C. (recrystallised from a mixture of petrol (b.p. 60°-80° C.) and ethyl acetate).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/ethyl acetate (17/3 v/v)

Sources & evidence

ORD record
ord-86023b20d24b40fcb63242d9e287e6bf
Source dataset
uspto-grants-1992_02
Patent number
US05089513

Reaction notes

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