HCID 57407850, compound → HCID 44629273, compound

HRID 731116Notes

Reaction equation

HRID 731116 reaction equation
[C:1]([Si:5]([O:8][C@H:9]([CH2:13][CH3:14])/[CH:10]=[CH:11]/I)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Si:15]([O:22][C@H:23]([C:31]#[C:32]/[CH:33]=[CH:34]/[CH:35]=[CH:36]/[C@H:37]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:38][C:39]#[CH:40])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>>[Si:15]([O:22][C@H:23]([C:31]#[C:32]/[CH:33]=[CH:34]/[CH:35]=[CH:36]/[C@H:37]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:43])[CH3:44])[CH2:38][C:39]#[C:40]/[CH:11]=[CH:10]/[C@H:9]([O:8][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:6])[CH3:7])[CH2:13][CH3:14])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])([C:18]([CH3:20])([CH3:19])[CH3:21])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 57407850HCID 57407850, compoundHCID 86760947HCID 86760947, compound

Product 1

HCID 44629273HCID 44629273, compoundYield 80%

Procedure

Sonogashira coupling between (R,E)-tert-butyl(1-iodopent-1-en-3-yloxy)dimethylsilane and (5S,8E,10E,12R)-methyl 5,12-bis(tert-butyldimethylsilyloxy)pentadeca-8,10-dien-6,14-diynoate (the product of Example 2 or Example 3), using a procedure analogous to that of Example 2, Step 1 gave the product in 80% yield. 1H NMR (500 MHz, C6D6): δ 6.59 (dd, J=15.2 Hz and 10.9 Hz, 1H), 6.24 (dd, J=15.2 and 11.0 Hz, 1H), 6.14 (dd, J=15.5 Hz and 5.3 Hz, 1H), 5.86 (d, J=15.4 Hz, 1H), 5.67 (dd, J=14.8 Hz and 5.6 Hz, 1H), 5.59 (d, J=15.5 Hz, 1H), 4.54 (t, J=5.7 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.94 (q, J=5.6 Hz, 1H), 3.35 (s, 3H), 2.46 (m, 2H), 2.17 (t, J=7.1 Hz, 2H), 1.84 (m, 4H), 1.44 (m, 2H), 1.04 (s, 9H), 1.02 (s, 9H), 1.00 (s, 9H), 0.86 (t, J=7.5 Hz, 3H), 0.28 (s, 3H), 0.19 (s, 3H), 0.14 (s, 3H), 0.08 (s, 3H), 0.07 (s, 3H), 0.05 (s, 3H). 13C NMR (125 MHz, C6D6): δ 173.131, 145.665, 141.248, 138.411, 129.420, 111.518, 109.904, 93.989, 87.526, 84.119, 81.048, 73.998, 72.025, 63.570, 50.913, 38.321, 33.587, 31.253, 29.235, 26.014, 21.163, 18.413, 9.221, −4.207, −4.421, −4.603, −4.621, −4.772, −5.094.

Workup

  1. customgave the product in 80% yield

Sources & evidence

ORD record
ord-30d23965438648fdad2165ccffb87289
Source dataset
uspto-grants-2009_09
Patent number
US07582785B2

Reaction notes

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