Phenylacetylene → (E)-(2-(hydroxymethyl)phenyl) dimethyl(2-phenylethenyl)silane

HRID 2423266Notes

Reaction equation

HRID 2423266 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Si:9]([CH3:19])([CH3:18])/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C#C)C=CC=CC=1.C[SiH](C)C1C=CC=CC=1COC1CCCCO1.C#CCCCCCC>CCCCCC.C(OCC)(=O)C>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Si:9]([CH3:18])([CH3:19])/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 10821PhenylacetyleneHCID 123701-OctyneHCID 11425884(E)-(2-(hydroxymethyl)phenyl)dimethyl(1-octenyl)silaneHCID 102158600dimethyl[2-(2-tetrahydro-2H-pyranoxymethyl)phenyl]silane

Product 1

HCID 11989414(E)-(2-(hydroxymethyl)phenyl) dimethyl(2-phenylethenyl)silaneYield 84%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The same operation as in the preparation of the compound 1a except that phenylacetylene (0.20 g, 2.0 mmol) was used instead of 0.55 g and 2.2 mmol of dimethyl[2-(2-tetrahydro-2H-pyranoxymethyl)phenylsilane (R2 and R3 in (5): methyl group) and 1-octyne, thereby obtaining (E)-(2-(hydroxymethyl)phenyl) dimethyl(2-phenylethenyl)silane (0.45 g, yield of 84%) as a colorless oil, Rf: 0.20 (hexane-ethyl acetate=10:1). 1H NMR (400 MHz, CDCl3) δ 7.62 (dd, J=7.4, 1.3 Hz, 1H), 7.51-7.41 (m, 4H), 7.37-7.27 (m, 4H), 6.97 (d, J=19.2 Hz, 1H), 6.67 (d, J=19.2 Hz, 1H), 4.79 (s, 2H), 0.52 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 145.2, 138.0, 136.4, 135.3, 130.0, 128.6, 128.3, 127.9, 127.8, 127.1, 126.5, 65.4, −1.2; Anal. Calcd for C17H20Osi; C, 76.07; H, 7.51. Found: C, 75.73; H, 7.55.

Sources & evidence

ORD record
ord-036b07609f2441a0bc454d67d9d23f07
Source dataset
uspto-grants-2011_06
Patent number
US07960571B2

Reaction notes

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