Triethylsilane → 2',3',5,6-tetrahydrospiro[benzo[1,2-b:5,4-b']difuran-3,8'-[1,4]dioxino[2,3-f]indol]-7'(6'H)-one

HRID 1407631Notes

Reaction equation

HRID 1407631 reaction equation
C1(C(C2C=CC=CC=2)[CH:8]2[O:12][C:11]3=[CH:13][C:14]4[O:15][CH2:16][C:17]5([C:31]=4[CH:32]=[C:10]3[CH2:9]2)[C:25]2[CH:24]=[C:23]3[O:26][CH2:27][CH2:28][O:29][C:22]3=[CH:21][C:20]=2[NH:19][C:18]5=[O:30])C=CC=CC=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[O:26]1[C:23]2=[CH:24][C:25]3[C:17]4([CH2:16][O:15][C:14]5[CH:13]=[C:11]6[C:10](=[CH:32][C:31]4=5)[CH2:9][CH2:8][O:12]6)[C:18](=[O:30])[NH:19][C:20]=3[CH:21]=[C:22]2[O:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 866974756-(diphenylmethyl)-2',3',5,6-tetrahydrospiro[benzo[1,2-b:5,4-b']difuran-3,8'-[1,4]dioxino[2,3-f]indol]-7'(6'H)-one

Product 1

HCID 593527262',3',5,6-tetrahydrospiro[benzo[1,2-b:5,4-b']difuran-3,8'-[1,4]dioxino[2,3-f]indol]-7'(6'H)-oneYield 23%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 6-(diphenylmethyl)-2′,3′,5,6-tetrahydrospiro[benzo[1,2-b:5,4-b′]difuran-3,8′-[1,4]dioxino[2,3-f]indol]-7′(6′H)-one (0.5 g, 1.0 mmol) in trifluoroacetic acid (7 mL) was added triethylsilane (0.47 mL, 3.0 mmol). The reaction mixture was heated at reflux for 3.5 h and concentrated in vacuo. The residue was triturated in methanol to afford 2′,3′,5,6-tetrahydrospiro[benzo[1,2-b:5,4-b′]difuran-3,8′-[1,4]dioxino[2,3-f]indol]-7′(6′H)-one (0.076 g, 23%) as a colorless solid: mp>250° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s, 1H), 6.61 (s, 1H), 6.50 (s, 1H), 6.40 (s, 1H), 6.36 (s, 1H), 4.66 (ABq, J=36.8, 9.2 Hz, 2H), 4.54-4.44 (m, 2H), 4.24-4.11 (m, 4H), 3.02-2.92 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.8, 160.8, 160.4, 143.3, 138.7, 135.4, 125.1, 120.9, 119.5, 118.9, 113.0, 99.0, 92.2, 79.7, 72.0, 64.2, 63.7, 57.1, 28.3; MS (ES+) m/z 337.9 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3.5 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in methanol

Sources & evidence

ORD record
ord-b27b1beed2214047888660ce9cdbde65
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…