Diisopropylamine → HCID 15086688, 화합물

HRID 359367

반응식

HRID 359367 반응식
[CH:1](NC(C)C)([CH3:3])[CH3:2].[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][C:14]1([CH3:21])[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[O:15]1.CC1C=CC([CH:27]=[S:28])=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.CCCCCC.C(N(CC)CC)C.CN(C)P(N(C)C)(N(C)C)=O>[CH3:13][C:14]1([CH3:21])[C:18](=[O:19])[CH:17]=[C:16](/[CH:20]=[CH:11]/[C:10]2[CH:3]=[CH:1][C:2]([S:28][CH3:27])=[CH:8][CH:9]=2)[O:15]1

참가 물질

10

반응물 5

HCID 7912DiisopropylamineHCID 9845Trifluoroacetic anhydrideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-HCID 181775354-MethylthiobenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 15086688HCID 15086688, 화합물수율 48%

시약·촉매·용매 4

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매HCID 8471Triethylamine용매HCID 12679Hexamethylphosphoramide용매

실험 절차

To a solution of dry diisopropylamine (5.0 mL, 35.7 mM) in dry tetrahydrofuran (150 mL) at -78° C., was added dropwise a 2.3N solution of n-butyllithium in hexane (15.5 mL, 35.7 mM). After the reaction solution was stirred for 15 minutes, a solution of 2,2,5-trimethyl-3(2H)-furanone (30 g, 23.8 mM) in tetrahydrofuran (25 mL) was added dropwise. Hexamethylphosphoramide (6.4 mL, 34.7 mM) was then added dropwise after 30 minutes. Finally, p-methylthiobenzaldehyde (43 g, 28.5 mM) in tetrahydrofuran (25 mL) was added in one portion. The reaction solution was stirred 15 minutes when trifluoroacetic anhydride (10.5 mL, 75 mM) was added in one portion. Again, the reaction solution was stirred 15 minutes when triethylamine (5.9 mL, 48 mM) was added and was allowed to warm to room temperature. Then the reaction mixture was partitioned between saturated aqueous sodium chloride (50 mL) and diethyl ether (50 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (2×25 mL) and saturated aqueous sodium chloride (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an amber liquid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford yellow crystals (3.0 g, 48% yield), m.p. 98°-99.5° C.

후처리

  1. additionwas added in one portion
  2. additionwas added
  3. customThen the reaction mixture was partitioned between saturated aqueous sodium chloride (50 mL) and diethyl ether (50 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium bicarbonate (2×25 mL) and saturated aqueous sodium chloride (25 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an amber liquid
  10. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

출처 및 근거

ORD 기록
ord-7f3bc3560564426f86104ae3191765ed
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001126

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