Veratryl alcohol → Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate

HRID 2099958

反応式

HRID 2099958 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1O)[C:17]([O:19][CH3:20])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][O:12][C:23]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[Cl:13]

参加物

6

反応物 4

HCID 7118Veratryl alcoholHCID 11776TriphenylphosphineHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 57796893Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (3,4-dimethoxyphenyl)methanol (6.0 g, 40 mmol) (Aldrich Chemical Co., Milwaukee, Wis.) and methyl 3-chloro-4-hydroxybenzoate (2.5 g, 13.5 mmol) (Lancaster Synthesis Ltd, Windham, N.H.) in THF (100 mL) was cooled to 0° C. and treated with triphenylphosphine (8.8 g, 33.5 mmol). A solution of diethylazodicarboxylate (5.3 mL, 33.5 mmol) in THF (50 mL) was added dropwise over 30 minutes. After the addition was complete, the reaction was warmed to room temperature and stirred for an additional 30 minutes, and then concentrated to orange oil. The crude reaction was applied directly to a silica column and flushed with hexanes. The desired product was eluted from the column using 25% EtOAc in Hexanes to afford 1A as a light yellow solid (2.5 g, 56%).

後処理

  1. additionAfter the addition
  2. concentrationconcentrated to orange oil
  3. customThe crude reaction
  4. customflushed with hexanes
  5. washThe desired product was eluted from the column

出典と根拠

ORDレコード
ord-d1f4d470a1d74677a7686f33a9dd5b5f
出典データセット
uspto-grants-2009_08
特許番号
US07569725B2

関連ノート

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