Boron trifluoride etherate → 3-(4-Benzyloxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic Acid

HRID 585195

반응식

HRID 585195 반응식
[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31](O)[C:32]([CH3:43])([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]([OH:35])=[O:34])=[CH:27][C:26]=1[O:45][CH3:46])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([CH3:43])([O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:33]([OH:35])=[O:34])=[CH:27][C:26]=1[O:45][CH3:46])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 223400103-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic Acid

생성물 1

HCID 223399703-(4-Benzyloxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic Acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-10 °C

실험 절차

A stirred solution of Et3SiH (8.67 mL, 54.3 mmol) in CH2Cl2 (45 mL) was treated with BF3-Et2O (6.8 mL, 54.3 mmol). 3-(4-Benzyloxy-3-methoxyphenyl)-3-hydroxy-2-methyl-2-phenoxypropionic acid (7.39 g, 18.1 mmol) in CH2Cl2 (90.5 mL) was then added dropwise via addition funnel, maintaining temperature below −7° C. After the addition was complete, the reaction was stirred for 1.5 h at −10° C., then quenched with 1 M NaOH (18.1 mL) and diluted with H2O (12 mL). 1N HCl was used to adjust pH to 4, followed by separation of layers. The aqueous layer was extracted with CH2Cl2 (2×15 mL), and combined organic layers were washed first with 1N HCl (15 mL), then H2O (15 mL), followed by drying over Na2SO4 and concentration to a gummy orange solid (6.86 g, 97%): MS (EI) 410.2 (M+NH4)+, 391.3 (M−H)−.

후처리

  1. temperaturemaintaining temperature below −7° C
  2. additionAfter the addition
  3. customquenched with 1 M NaOH (18.1 mL)
  4. additiondiluted with H2O (12 mL)
  5. customfollowed by separation of layers
  6. extractionThe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  7. washwere washed first with 1N HCl (15 mL)
  8. dry with materialby drying over Na2SO4 and concentration to a gummy orange solid (6.86 g, 97%)

출처 및 근거

ORD 기록
ord-77a0dfd0745141098203ac7c1b5db516
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930120B2

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