(Dimethyl sulfide)trihydroboron → Benzoic acid, 4,5-dichloro-2-(hydroxymethyl)-, methyl ester

HRID 1886467

반응식

HRID 1886467 반응식
[C:1]([C:5]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:6]=1[C:7](O)=[O:8])([O:3][CH3:4])=[O:2].B.CSC>C1COCC1>[Cl:15][C:11]1[C:12]([Cl:14])=[CH:13][C:5]([C:1]([O:3][CH3:4])=[O:2])=[C:6]([CH2:7][OH:8])[CH:10]=1

참가 물질

4

반응물 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 198042632-Carbomethoxy 4,5-dichlorobenzoic acid

생성물 1

HCID 19804259Benzoic acid, 4,5-dichloro-2-(hydroxymethyl)-, methyl ester수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the product of Step A (1.06 g, 4.28 mmol) in 5 mL of THF at 0° C. was added borane-methyl sulfide (6.42 mL of 2M solution in THF, 12.84 mmol, 3.0 eq). The reaction was allowed to warm to room temperature. After 16 hours the reaction was cooled to 0° C. and quenched with methanol. The volatiles were removed in vacuo and the oil flash chromatographed with 2:1 hexane/ethyl acetate to yield the titled compound (169 mg, 17%). Approximately 80% of the starting material was also recovered.

후처리

  1. temperatureAfter 16 hours the reaction was cooled to 0° C.
  2. customquenched with methanol
  3. customThe volatiles were removed in vacuo
  4. customthe oil flash chromatographed with 2:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-ccccee2330bc4a26867c41b2ed8763e7
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05151435

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