4-Ethynylheptan-4-ol → HCID 66629476, compound

HRID 341608Notes

Reaction equation

HRID 341608 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][CH2:10][NH:11]C(=O)C(F)(F)F)[CH:5]=[CH:6][CH:7]=1.[C:19]([C:21]([OH:28])([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])#[CH:20]>>[NH2:11][CH2:10][CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:20]#[C:19][C:21]([OH:28])([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[CH:3]=1)=[O:18]

Participants

3

Reactant 2

HCID 123838984-Ethynylheptan-4-olHCID 57608513HCID 57608513, compound

Product 1

HCID 66629476HCID 66629476, compound

Procedure

N-(3-(3-Bromophenyl)-3-oxopropyl)-2,2,2-trifluoroacetamide (63) was coupled with alkynol 20 following the procedure described in Example 18 except that the reaction was run at 80° C. for 3 h to give 3-amino-1-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)propan-1-one as a dark amber oil after purification by flash chromatography (20% EtOAc in hexanes). Yield (28.1 g, 99.6%). 1H NMR (400 MHz, DMSO-d6) δ 9.40 (br. t, 1H), 7.84-7.92 (m, 2H), 7.58-7.63 (m, 1H), 7.50 (t, J=7.6 Hz, 1H), 5.19 (s, 1H), 3.51 (q, J=5.7 Hz, 2H), 3.30 (t, J=6.7 Hz, 2H), 1.40-1.63 (m, 8H), 0.90 (t, J=7.2 Hz, 6H).

Sources & evidence

ORD record
ord-83db44bf87d748a0b1b1ed30eae1f008
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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