3-Iodobenzyl alcohol → HCID 58319087, compound

HRID 2042976Notes

Reaction equation

HRID 2042976 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].I[C:16]1[CH:17]=[C:18]([CH2:22][OH:23])[CH:19]=[CH:20][CH:21]=1>>[OH:23][CH2:22][C:18]1[CH:17]=[C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 423003-Iodobenzyl alcoholHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319087HCID 58319087, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and (3-iodophenyl)methanol (0.07 mL, 0.55 mmol) according to the general procedure IB to give 40 mg (32%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.24 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.53 (s, 1H), 7.46-7.43 (m, 3H), 7.34-7.32 (m, 2H), 7.19-7.16 (m, 2H), 4.69 (s, 2H), 3.66 (s, 3H), 2.98-2.93 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 1.83 (s, 1H); 13CNMR (CDCl3) δ 173.1, 141.1, 140.9, 131.7, 130.7, 130.0, 128.6, 128.3, 126.7, 123.6, 121.1, 89.4, 88.9, 64.9, 51.6, 35.4, 30.8; ESI-MS m/z 317.1 (MNa+).

Sources & evidence

ORD record
ord-ace43ba4d7da42039de24668563d67e5
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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