Dichloromethane → Ethyl 2,3-dichloro-4-(4'-hydroxybenzyl)phenoxyacetate

HRID 2166844ノート

反応式

HRID 2166844 の反応式
FC(F)(F)C(O)=O.[BH4-].[Na+].[Cl:10][C:11]1[C:23]([Cl:24])=[C:22]([C:25](=O)[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(Cl)Cl>O>[Cl:10][C:11]1[C:23]([Cl:24])=[C:22]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)[CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydride2 回HCID 12854007Ethyl 2,3-Dichloro-4-(4'-hydroxybenzoyl)phenoxyacetate

生成物 1

HCID 13145653Ethyl 2,3-dichloro-4-(4'-hydroxybenzyl)phenoxyacetate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To trifluoroacetic acid (50 ml.) under a nitrogen atmosphere was added 2.27 g. (0.06 mole) of NaBH4 pellets over a period of 30 minutes at 5°. A solution of ethyl 2,3-dichloro-4-(4'-hydroxybenzoyl)phenoxyacetate (prepared as described in Example 1) (3 g., 0.0081 mole) in 30 ml. of methylene chloride was added dropwise at 15°-20° over a period of 20 minutes. The reaction mixture was stirred overnight at room temperature while the NaBH4 pellets slowly dissolved. At this time the reaction mixture was poured into water and the resulting solution extracted with methylene chloride. The organic extract was washed with aqueous NaCL and dried over MgSO4. Evaporation of the methylene chloride furnished a residue which was chromatographed on a silica gel column eluting with increasing amounts of methanol (MeOH) in CH2Cl2. There was obtained 2 g. of white solid, m.p. 102°-103°.

後処理

  1. dissolutionslowly dissolved
  2. extractionthe resulting solution extracted with methylene chloride
  3. extractionThe organic extract
  4. washwas washed with aqueous NaCL
  5. dry with materialdried over MgSO4
  6. customEvaporation of the methylene chloride
  7. customfurnished a residue which
  8. customwas chromatographed on a silica gel column
  9. washeluting with increasing amounts of methanol (MeOH) in CH2Cl2
  10. customThere was obtained 2 g

出典と根拠

ORDレコード
ord-e458709b3e71419db3d894573d878321
出典データセット
uspto-grants-1983_06
特許番号
US04389416

反応ノート

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