1-Bromo-4-(methoxymethoxy)benzene → HCID 178497953, compound

HRID 1179472Notes

Reaction equation

HRID 1179472 reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[C:13]([C:21]([CH3:29])([CH3:28])[O:22][SiH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:12]=1[O:30][CH2:31][O:32][CH3:33])=[O:5].Br[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=1>>[C:24]([SiH2:23][O:22][C:21]([CH3:29])([CH3:28])[C:13]1[C:12]([O:30][CH2:31][O:32][CH3:33])=[C:11]([CH:7]2[CH2:8][CH2:9][CH2:10][CH:6]2[C:4]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=2)=[O:5])[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=1)([CH3:25])([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 104659191-Bromo-4-(methoxymethoxy)benzeneHCID 131726631HCID 131726631, compound

Product 1

HCID 178497953HCID 178497953, compoundYield 76.4%

Procedure

Use conditions analogous to those described in Step E of Examples 1A and 1B to couple (±)-2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-bis-methoxymethoxy-phenyl]-cyclopentanecarboxylic acid methoxy-methyl-amide (0.622 g, 1.25 mmol) and 1-bromo-4-methoxymethoxy-benzene (0.543 g, 2.50 mmol). Purify the material by silica gel chromatography eluting with Hex:EtOAc (90:10) to afford the subtitled product (0.549 g, 76%) as an oil. 1H NMR (CDCl3) δ 0.02 (s, 3H), 0.04 (s, 3H), 0.90 (s, 9H), 1.72-1.77 (m, 1H), 1.91-2.12 (m, 4H), 2.21-2.30 (m, 1H), 3.38 (s, 3H), 3.43 (s, 3H), 3.59 (s, 3H), 3.80-3.87 (m, 1H), 4.18-4.25 (m, 1H), 4.55 (dd, J=13.6, 44.7 Hz, 2H), 4.89 (dd, J=5.9, 7.5 Hz, 2H), 4.95 (dd, J=6.6, 20.3 Hz, 2H), 5.12 (dd, J=6.8, 7.9 Hz, 2H), 6.61 (d, J=3.0 Hz, 1H), 6.75 (d, J=3.0 Hz, 1H), 6.81 (d, J=8.9 Hz, 2H), 7.63 (d, J=8.9 Hz, 2H).

Workup

  1. customPurify the material by silica gel chromatography
  2. washeluting with Hex

Sources & evidence

ORD record
ord-808586ef4b8742ff930c10eb8553b83c
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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