Sodium hydride → Bisfarnesyl ether

HRID 68203

반응식

HRID 68203 반응식
[H-].[Na+].[CH3:3][C:4]([CH3:18])=[CH:5][CH2:6][CH2:7]/[C:8](/[CH3:17])=[CH:9]/[CH2:10][CH2:11]/[C:12](/[CH3:16])=[CH:13]/[CH2:14][OH:15]>C1COCC1>[CH2:14]([O:15][CH2:14][CH:13]=[C:12]([CH2:11][CH2:10][CH:9]=[C:8]([CH2:7][CH2:6][CH:5]=[C:4]([CH3:3])[CH3:18])[CH3:17])[CH3:16])[CH:13]=[C:12]([CH2:11][CH2:10][CH:9]=[C:8]([CH2:7][CH2:6][CH:5]=[C:4]([CH3:18])[CH3:3])[CH3:17])[CH3:16]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 445070Farnesol

생성물 1

HCID 57089234Bisfarnesyl ether수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
25 °C

실험 절차

To 81 mg (2.03 mmole, 2 eq) of 60% sodium hydride (washed with anhydrous hexanes to remove mineral oil) in 1 mL of anhydrous THF under an argon atmosphere at 0° C., 228 mg (1.02 mmol) of trans,trans-farnesol in 1 mL of anhydrous THF was added. The mixture was stirred for 10 min, then 438 mg (1.53 mmol, 1.5 eq) of trans,trans-farnesol bromide was added in 0.5 ml of anhydrous THF. The mixture was stirred for 20 h and allowed to warm to 25° C. The reaction was quenched with 2 mL of 1M HCl, diluted with EtOAc, washed successively with water and brine and dried over anhydrous MgSO4. The crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc:hexanes to afford 174 mg (40%) of bisfarnesyl ether that had NMR and mass spectral data identical to that of material produced in enzymatic reactions (FIG. 7).

후처리

  1. stirringThe mixture was stirred for 20 h
  2. customThe reaction was quenched with 2 mL of 1M HCl
  3. additiondiluted with EtOAc
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe crude product was chromatographed on silica gel F254 preparative TLC plates (Merck) in 1:10 EtOAc

출처 및 근거

ORD 기록
ord-9086d4653b814db0872f256be1da7b5e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822187B1

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