Bromobenzene → [5-(2,6-Dimethyl-4-triisopropylsilanyloxy-benzyl)-2-methoxymethoxy-phenyl]-phenyl-methanol

HRID 2108636Notes

Reaction equation

HRID 2108636 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:13][C:14]1[CH:32]=[C:31]([O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[CH:30]=[C:29]([CH3:44])[C:15]=1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][O:27][CH3:28])=[C:21]([CH:24]=1)[CH:22]=[O:23]>C1COCC1>[CH3:44][C:29]1[CH:30]=[C:31]([O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:35]([CH3:37])[CH3:36])[CH:38]([CH3:40])[CH3:39])[CH:32]=[C:14]([CH3:13])[C:15]=1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][O:27][CH3:28])=[C:21]([CH:22]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:23])[CH:24]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 866034575-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 66642871[5-(2,6-Dimethyl-4-triisopropylsilanyloxy-benzyl)-2-methoxymethoxy-phenyl]-phenyl-methanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirring solution of bromobenzene (0.45 g, 2.89 mmol) in THF (20 mL) at −78° C. was added n-BuLi (1.16 mL, 2.5 M in hexanes). The mixture was stirred at −78° C. for 1 h and a solution of 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde (example 35; step e, 1.2 g, 2.63 mmol) was added. The reaction mixture was stirred at −78° C. for 1 h, allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with saturated NH4Cl and diluted with diethyl ether. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford [5-(2,6-dimethyl-4-triisopropylsilanyloxy-benzyl)-2-methoxymethoxy-phenyl]-phenyl-methanol as an yellow oil (1.4 g, 99.6%): 1H NMR (200 MHz, DMSO-d6): δ 7.23 (m, 6 H), 6.85 (d, J=8.8 Hz, 1 H), 6.68 (m, 1 H), 6.56 (s, 2 H), 5.92 (d, J=4.0 Hz, 1 H), 5.62 (d, J=4.0 Hz, 1 H), 5.10 (q, J=4.0 Hz, 2 H), 3.84 (s, 2 H), 3.23 (s, 3 H), 2.11 (s, 6 H), 1.23 (m, 3 H), 1.06 (d, J=6.4 Hz, 18 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=15% ethyl acetate in hexanes; Rf=0.50.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 h
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction mixture was quenched with saturated NH4Cl
  5. additiondiluted with diethyl ether
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97221937912e42c98cb058917bfa1264
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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