Benzyl Bromide → (2S,4S) Benzhydryl 2-Benzyl-4-(2-furyl)-3-oxaoctanoate

HRID 5562

반응식

HRID 5562 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([CH2:25][CH2:26][CH2:27][CH3:28])[O:7][CH2:8][C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH2:39]([C@H:8]([O:7][C@H:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:26][CH2:27][CH3:28])[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 20093117Benzhydryl 4-(2-furyl)-3-oxaoctanoate

생성물 1

HCID 70061125(2S,4S) Benzhydryl 2-Benzyl-4-(2-furyl)-3-oxaoctanoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
0 °C

실험 절차

Benzhydryl 4-(2-furyl)-3-oxaoctanoate (2.0 g, 5.28 mmol) was dissolved in 20 mL freshly distilled THF and cooled to -80°±5° C. under dry argon. Sodium bis(trimethylsilyl)-amide (1.0M in THF, 5.6 mL, 5.6 mmol) was slowly added keeping the temperature at -80°±5° C. After 15 m, freshly distilled and filtered (through basic alumina) benzyl bromide (0.7 mL, 5.81 mmol) in HMPA (4 mL) was added dropwise maintaining the reaction temperature at -75°±5 ° C. After 15 m, the reaction was allowed to warm to 0° C. for 1 h before quenching with water and extraction with ether. The combined ether extracts were washed with saturated NH4Cl, 5% NaHCO3, brine,dried over MgSO4, and purified by flash silica gel chromatography to give 771.3 mg (31%): [α]25D - 65.5°; 1H NMR (300 MHz, CDCl3) δ 0.81 (t, 3H, J=7 Hz), 1.22 (m, 4H), 1.80 (m, 2H), 2.91 (m, 2H), 4.12 (dd, 1H, J=9 Hz), 4.30 (t, 1H, J=7 Hz), 5.86 (m, 1H), 6.19 (m, 1H), 6.69

후처리

  1. temperaturecooled to -80°±5° C. under dry argon
  2. customat -80°±5° C
  3. distillationAfter 15 m, freshly distilled
  4. additionwas added dropwise
  5. temperaturemaintaining the reaction temperature at -75°±5 ° C
  6. custombefore quenching with water and extraction with ether
  7. washThe combined ether extracts were washed with saturated NH4Cl, 5% NaHCO3, brine,dried over MgSO4
  8. custompurified by flash silica gel chromatography
  9. customto give 771.3 mg (31%)
  10. custom[α]25D - 65.5°

출처 및 근거

ORD 기록
ord-ad9cc210d01d4d0d92c70ab465fa4799
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244910

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