Water → 1-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene

HRID 2255030Notes

Reaction equation

HRID 2255030 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Li]CCCC.[Si:15]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]I)=[CH:26][CH:25]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>C1COCC1.CCOCC>[Si:15]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:26][CH:25]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 962Water2×HCID 189371-NonyneHCID 107373351-[(tert-Butyldimethylsilyl)oxymethyl]-4-iodomethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 197395361-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzeneYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1; -nonyne (150 mg, 1.2 mmol) in THF (5 mL) at -78° C., was added n-BuLi (0.47 mL, 1.19 mmol). The resulting mixture was stirred for 30 minutes and a solution of [(tertButyldimethylsilyl)oxymethyl]-4-iodomethyl benzene (40) (361 mg, 2 mmol) in THF (1 mL) was added. The reaction mixture was then stirred at -78° C. for 1 hour, allowed to warm to 0° C. and stirred for an additional 30 minutes. At this time, water (2 mL) was slowly added and the mixture was poured into water (50 mL) and Et2O (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to yield a yellow oil. Purification by flash silica gel chromatography (95:05 hexane/EtOAc) afforded (51) (313 mg, 87%) as a colorless oil: Rf 0.85 (95:05 hexane/EtOAc); 1H NMR (CDCl3) δ 7.34 (d, J=8.7 Hz, 2 H), 7.29 (d, J=7.8 Hz, 2 H), 4.75 (s, 2 H), 3.59 (t, J=2.4 Hz, 2 H), 2.24 (tt, J1 =7.2 Hz, J2 =2.4 Hz, 2 H), 1.55 (m, 2 H), 1.42 (m, 2 H), 1.32 (m, 6 H), 0.97 (s, 9 H), 0.92 (t, J=6.9 Hz, 3 H), 0.12 (s, 6 H); 13 C NMR (CDCl3) δ 139.68, 136,38, 127.83, 126.32, 82.74, 77.76, 64.93, 31.91, 29.18, 29.98, 26.08, 24.97, 22.77, 18.97, 14.23, -5.11. ##STR25##

Workup

  1. stirringThe reaction mixture was then stirred at -78° C. for 1 hour
  2. stirringstirred for an additional 30 minutes
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a yellow oil
  7. customPurification by flash silica gel chromatography (95:05 hexane/EtOAc)

Sources & evidence

ORD record
ord-00db919125594a219645b68a46d36a53
Source dataset
uspto-grants-1993_08
Patent number
US05238832

Reaction notes

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