Propargyl alcohol → Tert-butyl 3-hydroxy-3-(3-(3-hydroxyprop-1-ynyl)phenyl)propylcarbamate

HRID 658845Notes

Reaction equation

HRID 658845 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.[CH2:20]([OH:23])[C:21]#[CH:22]>>[OH:19][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:22]#[C:21][CH2:20][OH:23])[CH:3]=1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 7859Propargyl alcoholHCID 57608439Tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate

Product 1

HCID 66743507Tert-butyl 3-hydroxy-3-(3-(3-hydroxyprop-1-ynyl)phenyl)propylcarbamate

Procedure

Sonogashira reaction of bromide 39 with propargyl alcohol gave tert-butyl 3-hydroxy-3-(3-(3-hydroxyprop-1-ynyl)phenyl)propylcarbamate as brown oil. Yield (0.880 g, 94%): 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.28-7.36 (m, 3H), 4.85-4.87 (bs, 1H), 4.70-4.72 (m, 1H), 4.49 (d, J=5.2 Hz, 2H), 3.47-3.50 (m, 1H), 3.44 (bs, 1H), 3.12-3.17 (m, 1H), 1.93-1.99 (m, 2H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-53f9a187cf344b1d9305391f28ca5492
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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