Ethyl Acetate → (2-Methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

HRID 1865143ノート

反応式

HRID 1865143 の反応式
[OH:1][CH2:2][C:3]1([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:7][O:6][C:5]([CH3:8])=[N:4]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCOC(C)=O>CN(C=O)C.O>[CH3:8][C:5]1[O:6][CH2:7][C:3]([CH2:2][OH:1])([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:15][CH:16]=2)[N:4]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 579352584-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

生成物 1

HCID 66768869(2-Methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of 4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (300 mg, 1.27 mmol) in DMF (5 ml) was added Cs2CO3 (1.2 g, 3.83 mmol) and (3-bromo-propoxy)-benzene (273 mg, 1.27 mmol). The reaction mixture was stirred at 85° C. for 4 hours. AcOEt and water were then added, the organic layer was separated and the aqueous phase was extracted with AcOEt (3×50 ml). The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (AcOEt/Hexane 9:1) affords (2-methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol as colorless oil. To a solution of (2-methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol (50 mg, 0.135 mmol) in ethanol (2 ml) was added conc. HCl (2 ml). The reaction mixture was stirred at 85° C. for 2 hours, then concentrated to dryness. The residue was re-dissolved in AcOEt and precipitated with hexanes. The solid was filtered off, washed with dry ether and dried in vacuo to afford 2-amino-2-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-propane-1,3-diol hydro-chloride as a colorless powder. ESI+ MS: m/z=370.4 (M+H)+.

後処理

  1. customthe organic layer was separated
  2. extractionthe aqueous phase was extracted with AcOEt (3×50 ml)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customPurification by flash chromatography (AcOEt/Hexane 9:1)

出典と根拠

ORDレコード
ord-8edd15f156a04ff4a5a0350957d8dd1c
出典データセット
uspto-grants-2009_12
特許番号
US07625950B2

反応ノート

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