Lithium hydroxide, monohydrate → 2-[4-(Dimethoxy-phosphoryl)-but-2-enyl]-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enoic Acid

HRID 272129

반응식

HRID 272129 반응식
C[O:2][C:3](=[O:34])[CH:4]([CH2:24][CH:25]=[CH:26][CH2:27][P:28]([O:32][CH3:33])([O:30][CH3:31])=[O:29])[CH2:5][C:6]([CH3:23])=[CH:7][CH2:8][C:9]1[C:10]([OH:22])=[C:11]2[C:15](=[C:16]([CH3:20])[C:17]=1[O:18][CH3:19])[CH2:14][O:13][C:12]2=[O:21].O[Li].O>O.CO.C1COCC1>[CH3:31][O:30][P:28]([CH2:27][CH:26]=[CH:25][CH2:24][CH:4]([CH2:5][C:6]([CH3:23])=[CH:7][CH2:8][C:9]1[C:10]([OH:22])=[C:11]2[C:15](=[C:16]([CH3:20])[C:17]=1[O:18][CH3:19])[CH2:14][O:13][C:12]2=[O:21])[C:3]([OH:34])=[O:2])([O:32][CH3:33])=[O:29]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrate2회HCID 765461882-[4-(Dimethoxy-phosphoryl)-but-2-enyl]-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enoic acid methyl ester

생성물 1

HCID 765461892-[4-(Dimethoxy-phosphoryl)-but-2-enyl]-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enoic Acid

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

2-[4-(Dimethoxy-phosphoryl)-but-2-enyl]-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enoic acid methyl ester (460 mg, 0.927 mmol) in a solution of 1:1:2 of H2O/MeOH/THF (8 mL) was stirred with LiOH.H2O (78 mg, 1.86 mmol) at ambient temperature for 12 hours. A second batch of LiOH.H2O (40 mg, 0.952 mmol) was added. The reaction mixture was stirred at room temperature for another 16 hours, after which no further progress was observed. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl. The organic layer was removed in vacuo and the product was extracted with EtOAc from the aqueous layer, which had been acidified by addition of 5 drops of 2 N HCl. The product was further purified by chromatography to provide the desired product. 1H NMR (300 MHz, CDCl3) δ 1.79 (s, 3H), 2.08-2.38 (m, 4H), 2.15 (s, 3H), 2.53 (d, 1H, J=22 Hz), 2.60 (d, 1H, J=22 Hz), 2.57-2.64 (m, 1H), 3.38 (d, 2H, J=7 Hz), 3.72 (d, 6H, J=11 Hz) 3.76 (s, 3H), 5.20 (s, 2H), 5.27 (t, 1H, J=6 Hz), 5.36-5.63 (m, 2H); 31P (121.4 MHz, CDCl3) δ 30.5; MS (m/z) 481.2 [M−H]−.

후처리

  1. customThe reaction was quenched by addition of a saturated aqueous solution of NH4Cl
  2. customThe organic layer was removed in vacuo
  3. extractionthe product was extracted with EtOAc from the aqueous layer, which
  4. additionhad been acidified by addition of 5 drops of 2 N HCl
  5. customThe product was further purified by chromatography

출처 및 근거

ORD 기록
ord-617d8ced94e742da88a4b9a05509d0e7
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452901B2

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