Benzcatechinborane → (S)-ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate

HRID 926135노트

반응식

HRID 926135 반응식
[CH3:1][C:2]1[C:3]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[B]1OC2C(=CC=CC=2)O1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([C@H:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:19])([F:20])[F:18])(=[O:15])=[O:16])[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

4

반응물 2

HCID 6327445BenzcatechinboraneHCID 89676862Ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

생성물 1

HCID 89681708(S)-ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a solution of ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (3.93 g, 9.72 mmol) and (R)-2-methyl-CBS-oxazaoborolidine (0.539 g, 1.94 mmol) in anhydrous toluene (30 mL) at −40° C. was added dropwise a solution of catecholborane (1.40 mL, 13.22 mmol) in toluene (5 mL) over 20 minutes to give a pale yellow reaction mixture. The reaction mixture was stirred for another 20 minutes and quenched with saturated sodium carbonate solution and ethyl acetate was added. The mixture was stirred for 30 minutes, the aqueous layer removed and the organic layer washed with saturated sodium carbonate solution (3×), brine and dried (MgSO4) and filtered. Concentration and purification by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) gave the desired product. LCMS-ESI+ (m/z): [M+Na]+ calcd for C17H17F3NaO6S: 429.37. Found: 428.8.

후처리

  1. customto give a pale yellow reaction mixture
  2. customquenched with saturated sodium carbonate solution and ethyl acetate
  3. additionwas added
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe aqueous layer removed
  6. washthe organic layer washed with saturated sodium carbonate solution (3×), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationConcentration and purification by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b302c338847a408696d055d896cbedc4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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