1,2-Dichloroethane → 1-tert-butyl-6-methoxy-3H-pyrano[3,4-b][1]benzofuran-3-one

HRID 2103770Notes

Reaction equation

HRID 2103770 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[O:6][C:7]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:8]=2[C:9]=1[CH2:10][C:11]([OH:13])=[O:12])=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:2]([C:3]1[O:12][C:11](=[O:13])[CH:10]=[C:9]2[C:8]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:7]=3[O:6][C:5]=12)([CH3:21])([CH3:20])[CH3:1]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57804476[2-(2,2-Dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid

Product 1

HCID 578044781-tert-butyl-6-methoxy-3H-pyrano[3,4-b][1]benzofuran-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 98 mg [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]acetic acid from the Step B Example 1, 176 μL DIEA, and 114 mg HOBt in 3.5 mL dry DMF. Add 97.1 mg EDC and let the mixture stir at room temperature over night. It was purified directly on RP-HPLC using 50-70% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound as yellow solid. 1H NMR (CDCl3, 500 MHz) 7.34 (dd, J=1.3 & 8.4 Hz, 1H), 7.25˜7.29 (m, 2H), 6.54 (s, 1H), 3.92 (s, 3H), 1.52 (s, 9H). LC-MS: 3.55 min. (M+H=273.1).

Workup

  1. customIt was purified directly on RP-HPLC using 50-70% MeCN gradient
  2. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-db9f4483c3c1486ca8f73d316d5a9f05
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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