Diisopropylethylamine → Phosphorous acid mono-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl} ester

HRID 540738

반응식

HRID 540738 반응식
[OH:1][CH2:2][C:3]([CH3:26])=[CH:4][CH2:5][C:6]1[C:14]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:13]2[C:9]([CH2:10][O:11][C:12]2=[O:22])=[C:8]([CH3:23])[C:7]=1[O:24][CH3:25].CCN(C(C)C)C(C)C.Cl[P:37]1[O:42]C(=O)C2C=CC=CC=2[O:38]1>O1CCOCC1>[CH3:25][O:24][C:7]1[C:8]([CH3:23])=[C:9]2[C:13]([C:12](=[O:22])[O:11][CH2:10]2)=[C:14]([O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[C:6]=1[CH2:5][CH:4]=[C:3]([CH3:26])[CH2:2][O:1][P:37]([OH:42])[OH:38]

참가 물질

5

반응물 3

HCID 81531Diisopropylethylamine2회HCID 2370102-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one2회HCID 670102606-(4-Hydroxy-3-methyl-but-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-one

생성물 1

HCID 67010409Phosphorous acid mono-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl} ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 6-(4-hydroxy-3-methyl-but-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (75 mg, 0.20 mmol) and DIEA (49 μL, 0.28 mmol) in dioxane (2 mL) was added 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one (56.7 mg, 0.28 mmol) according the procedure of Shadid, B. et al., Tetrahedron, 1989, 45, 12, 3889. After 10 minutes, another portion of 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one (40 mg, 0.20 mmol) and DIEA (35 μL, 0.20 mmol) were added. The reaction was allowed to proceed at room temperature for an additional hour, after which it was quenched by the addition of H2O. The solution was stirred for another 10 minutes and concentrated in vacuo to a small volume. The product was triturated with diethyl ether and coevaporated from acetonitrile (4×10 mL) to provide the product. 1H NMR (300 MHz, CDCl3) δ 0.03 (s, 9H), 1.08-1.30 (m, 2H), 1.84 (br s, 3H), 2.17 (s, 3H), 3.46 (br s, 2H), 3.76 (s, 3H), 4.21-4.39 (m, 4H), 5.12 (s, 2H), 5.43-5.60 (m, 1H), 7.83 (br s, 1H); 31P (121.4 MHz, CDCl3) δ 7.22; MS (m/z) 441 [M−H]−.

후처리

  1. waitto proceed at room temperature for an additional hour
  2. customafter which it was quenched by the addition of H2O
  3. concentrationconcentrated in vacuo to a small volume
  4. customThe product was triturated with diethyl ether
  5. customto provide the product

출처 및 근거

ORD 기록
ord-ef4895a9b3af46578c030679cf7f389b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871785B2

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