1,3-Butadienyl acetate → HCID 15370489, compound

HRID 1598434Notes

Reaction equation

HRID 1598434 reaction equation
[CH2:1]([CH:4]1[C:9]2[C:10](=[O:15])[CH:11]=[CH:12][C:13](=[O:14])[C:8]=2[CH2:7][CH:6]([C:16]([O:18][CH3:19])=[O:17])[O:5]1)[CH2:2][CH3:3].O([CH:24]=[CH:25][CH:26]=[CH2:27])C(C)=O>>[CH2:1]([CH:4]1[C:9]2[C:10](=[O:15])[C:11]3[C:12]([C:13](=[O:14])[C:8]=2[CH2:7][CH:6]([C:16]([O:18][CH3:19])=[O:17])[O:5]1)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 151951,3-Butadienyl acetateHCID 18932666HCID 18932666, compound

Product 1

HCID 15370489HCID 15370489, compoundYield 71.9%

Procedure

The 1-propyl-3methoxycarbonyl-3,4,5,8-tetrahydro-5,8-dioxo-1H-benzo-[2,3-c]-pyran described in step 3 (76 mg, 0.288 mmol) was stirred with 1-acetoxyl-1,3-butadiene (136 μl, 1.152 mmol) at 45° C. for 20 hours. Solvent was evaporated and the crude product was chromatographed (toluene/ethyl acetate ~100/15, v/v) to give the titled compound (65 mg, 71.9%). m.p. 111.5°-113.6° C. 1H NMR (CDCl3, 250 MHz, Bruker), δ: 0.97 (3H, tr, J=6.7 Hz, CH3), 1.45-1.85 (4H, m, CH2CH2) 2.78 (1H, ddd, J=19.9 Hz, 10.4 Hz, 1.2 Hz, 4-Ha), 2.97 (1H, dd, J=19.9 Hz, 5.4 Hz, 7-He), 3.80 (3H, s, OCH3), 4.51 (1H, dd, J=10.4 Hz, 5.4 Hz, 3-H), 5.04 (1H, br d, J=8.5 Hz, 1-H), 7.72 (2H, m, 7, 8-ArH), 8.07 (2H, m 6, 9-ArH).

Workup

  1. customSolvent was evaporated
  2. customthe crude product was chromatographed (toluene/ethyl acetate ~100/15

Sources & evidence

ORD record
ord-7c404011d93b4a0eaff000dddb074f16
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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