Heptanoic acid, 6-oxo-, methyl ester → (R)-methyl 6-hydroxyheptanoate

HRID 628941노트

반응식

HRID 628941 반응식
O1CCCC1.B.[O:7]=[C:8]([CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]>C1(C)C=CC=CC=1>[OH:7][C@H:8]([CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

참가 물질

4

반응물 2

HCID 288022Heptanoic acid, 6-oxo-, methyl esterHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 118036747(R)-methyl 6-hydroxyheptanoate수율 51%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

(S)-methyloxazaborolidine (8.77 g, 31.63 mmol) dissolved in 30 mL of toluene. The solution was cooled to 0° C. and the borane tetrahydrofuran complex (31.6 mL of 1.0M solution in THF, 31.6 mmol) was added. After 30 min the ketone 24 (5.0 g, 31.63 mmol) was added. The reaction solution was stirred for 4 h and was then quenched by slow addition of saturated aqueous ammonium chloride. The resultant mixture was extracted with EtOAc (2×). The combined organic portions were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 3:1 hex/EtOAc) afforded 2.58 g (51%) of the alcohol 25 (see scheme 4).

후처리

  1. customwas then quenched by slow addition of saturated aqueous ammonium chloride
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-661c1355917d4907b5abac8407e8f3fe
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315486B2

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