2-Bromomethylnaphthalene → HCID 9838161, compound

HRID 2303452Notes

Reaction equation

HRID 2303452 reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH:7]=[CH:8][CH2:9][CH:2]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1>C1COCC1>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][CH:4]1[C:5](=[O:6])[O:1][CH:2]2[CH2:9][CH:8]=[CH:7][CH:3]12

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 45828772H-Cyclopenta[b]furan-2-one, 3,3a,6,6a-tetrahydro-

Product 1

HCID 9838161HCID 9838161, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to the procedure of Example 1, the title compound was prepared from 7.4 g (59.6 mmol) of 3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one, 60 ml of a 1 molar lithium bis-(trimethylsilyl)-amide solution in THF and 13.2 g (59.7 mmol) of 2-(bromomethyl)-naphthalene in 180 ml of THF. Chromatographic purification is carried out using a mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4. Yield: 10.6 g (67.3%), pale yellow oil, diastereomeric mixture: 2.5:1 (Example 7). MS (ESI)[m/e]: 287 [M+Na+]

Workup

  1. customChromatographic purification
  2. additiona mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4

Sources & evidence

ORD record
ord-b057d57126834d51b80937fe1c90acc3
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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