Iodobenzene → HCID 16074360, compound

HRID 1815120Notes

Reaction equation

HRID 1815120 reaction equation
I[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.IC1C=CC=CC=1.[CH2:16]([C:20]1([CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[O:25][C:24](=[O:26])[CH:23]=[C:22]([O:27][CH2:28][CH3:29])[CH2:21]1)[CH2:17][C:18]#[CH:19].C(C1(C2CCCC2)OC(=O)CC(=O)C1)CC#C>>[CH:30]1([C:20]2([CH2:16][CH2:17][C:18]#[C:19][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=3)[O:25][C:24](=[O:26])[CH:23]=[C:22]([O:27][CH2:28][CH3:29])[CH2:21]2)[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

5

Reactant 4

HCID 11575IodobenzeneHCID 122723-IodophenolHCID 16074350HCID 16074350, compoundHCID 22499801HCID 22499801, compound

Product 1

HCID 16074360HCID 16074360, compound

Procedure

The title compound was prepared analogously to Example 6, except 3-iodophenol was used for iodobenzene, and 6-but-3-ynyl-6-cyclopentyl-4-ethoxy-5,6-dihydro-pyran-2-one, described in Step 2 of that example, was used for 6-but-3-ynyl-6-cyclopentyl-dihydro-pyran-2,4-dione. 1H NMR (CDCl3): δ 1.26 (t, 2H, J=7.16 Hz), δ 1.51-1.81 (m, 8H), δ 2.10 (t, 2H, J=7.54 Hz), δ 2.36 (t, 1H, J=8.10 Hz), δ 2.48 (d, 1H, J=17.71 H), δ 2.52 (t, 2H, J=7.35 Hz), δ 2.68 (d, 1H, J=17.52 Hz), δ 3.94 (q, 2H, J=7.35 Hz), δ 5.14 (d, 2H, J=6.22 Hz), δ 6.77 (dd, 1H, J=5.65 Hz, J=2.45 Hz), δ 6.87 (s, 1H), δ 6.95 (d, 1H, J=6.59 Hz), δ 7.14 (t, 1H, J=7.91 Hz). Anal. Calcd. For C22H26O4 0.3 EtOAc: C, 73.16, H 7.52. Found: C, 73.18, H, 7.57; ESIMS (M+Na+) 377.1.

Sources & evidence

ORD record
ord-408e7820b7d045318a42be33d35a3915
Source dataset
uspto-grants-2005_04
Patent number
US06878727B2

Reaction notes

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