4-Ethynylheptan-4-ol → HCID 57608493, compound

HRID 1618399Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([CH3:19])([CH3:18])[CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:6][CH:7]=1.[C:20]([C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])#[CH:21]>>[F:14][C:13]([F:16])([F:15])[C:12]([NH:11][CH2:10][C:9]([CH3:19])([CH3:18])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:21]#[C:20][C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH:3]=1)=[O:17]

Participants

Reactant 2

HCID 123838984-Ethynylheptan-4-ol

HCID 57608490HCID 57608490, compound

Product 1

HCID 57608493HCID 57608493, compound

Procedure

N-(3-(3-bromophenyl)-2,2-dimethylpropyl)-2,2,2-trifluoroacetamide (30) (0.489 g, 1.45 mmol) was coupled with 4-ethynylheptan-4-ol (20) (0.28 g, 2.0 mmol) following the method described in Example 15 and the product was purified by flash chromatography (0 to 50% EtOAc-hexanes gradient) to give 2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)-2,2-dimethylpropyl)acetamide (31) as a yellow oil. Yield (0.350 g, 61%): 1H NMR (400 MHz, CD3OD) δ 7.20-7.25 (m, 3H), 7.12-7.15 (m, 1H), 3.19 (s, 2H), 2.54 (s, 2H), 1.58-1.71 (m, 8H), 0.98 (t, J=7.2 Hz, 6H), 0.85 (s, 6H).

Workup

customthe product was purified by flash chromatography (0 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record: ord-83c6bc507ca341e5a8b260e34f7fd289
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08766007B2

Reaction notes

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