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

HRID 2166844노트

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HRID 2166844 반응식
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]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydride2회HCID 12854007Ethyl 2,3-Dichloro-4-(4'-hydroxybenzoyl)phenoxyacetate

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-e458709b3e71419db3d894573d878321
출처 데이터셋
uspto-grants-1983_06
특허 번호
US04389416

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