Benzyl Alcohol → 2-Benzyloxy-3-methoxybenzoic acid methyl ester

HRID 841785ノート

反応式

HRID 841785 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[OH:13].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 80651Methyl 3-methoxysalicylateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 698916402-Benzyloxy-3-methoxybenzoic acid methyl ester収率 58.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 3-methoxysalicylate (1.0 g, 5.49 mmol) in 5 ml tetrahydrofuran and 5 ml dimethylformamide was added sequentially at room temperature, benzyl alcohol (0.71 ml, 6.86 mmol), triphenylphosphine (2.16 g, 8.23 mmol) and diethyl azodicarboxylate (1.3 ml, 8.23 mmol). The reaction solution was stirred at room temperature overnight, then ethyl acetate was added and the resulting solution was washed sequentially with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was triturated with diethyl ether and filtered to remove triphenylphosphine oxide. The ether solution was concentrated to dryness in vacuo and the residue was purified by column chromatography on silica gel, eluting with 95:5 hexane/ethyl acetate, yielding the title compound as an oil (870 mg 58% yield). MS (M+1)+273.1

後処理

  1. washthe resulting solution was washed sequentially with water and brine
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness in vacuo
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered
  6. customto remove triphenylphosphine oxide
  7. concentrationThe ether solution was concentrated to dryness in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with 95:5 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-ca4fb8f88bff4678b867e64b7063c2e3
出典データセット
uspto-grants-2002_04
特許番号
US06369075B1

反応ノート

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