Sodium Bicarbonate → 1-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol

HRID 547076노트

반응식

HRID 547076 반응식
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH2:15]([C:17]([C:35]1[CH:48]=[CH:47][C:38]([O:39][CH2:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[C:37]([CH3:49])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:15]([C:17]([C:35]1[CH:48]=[CH:47][C:38]([O:39][CH2:40][CH:41]([OH:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[C:37]([CH3:49])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:27][C:28]([CH3:33])([CH3:34])[C:29]([CH3:31])([CH3:32])[O:30]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 3611392Lithium tri-s-butylborohydrideHCID 574435241-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one

생성물 1

HCID 574435301-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of lithium tri-sec-butylborohydride in tetrahydrofuran (1.06 M, 0.178 mL, 0.189 mmol) was added to a solution of 1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (Example 143-(4); 75.2 mg, 0.157 mmol) in tetrahydrofuran (3 mL) at −78° C., and the mixture was stirred for 30 minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (46.6 mg, 62%).

후처리

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-b64ed16a644c4628ba6a054020e6fc11
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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