2-Bromomethylnaphthalene → HCID 18461544, compound

HRID 2303449Notes

Reaction equation

HRID 2303449 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]1[C:15](=[O:16])[CH2:14][CH:13]2[CH2:17][CH2:18][CH2:19][CH:12]12.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH2:30]Br>C1COCC1>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH2:30][CH:14]1[C:15](=[O:16])[O:11][CH:12]2[CH2:19][CH2:18][CH2:17][CH:13]12

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 11665410hexahydro-cyclopenta[b]furan-2-one

Product 1

HCID 18461544HCID 18461544, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, 8.7 ml of a 1 molar solution of lithium bis-(trimethylsilyl)-amide in THF are added dropwise to a solution, cooled to −78° C., of 1 g (7.9 mmol) of hexahydro-cyclopenta[b]furan-2-one in 20 ml of THF such that the temp. of the mixture does not exceed −65° C. After the addition has ended, stirring is continued at −78° C. for 10 min, and 1.93 g (8.7 mmol) of naphth-2-ylmethyl bromide are then added in one portion. Immediately afterwards, the cooling bath is removed and the mixture is allowed to warm to room temp. After 16 h of stirring at room temp., the mixture is taken up in water/diethyl ether and the aqueous phase is extracted twice with diethyl ether. The combined organic phases are dried over sodium sulphate and then concentrated. The residue is chromatographed over silica gel (mobile phase: dichloromethane); Yield: 1.2 g, colourless oil, diastereomer mixture: 87:13 (Example 1) 1H-NMR (200 MHz; [d6]-DMSO): δ[ppm]=1.2-1.9 (br m,7H), 2.6 (m,1H), 2.87 (dd, 1H); 2.93 (dd,1H), 4.72/4.75 (m;1H), 7.48-7.55 (m;3H), 7.76 (s;1H), 7.81-7.95 (m;3H).

Workup

  1. customdoes not exceed −65° C
  2. additionAfter the addition
  3. customImmediately afterwards, the cooling bath is removed
  4. stirringAfter 16 h of stirring at room temp.
  5. extractionthe aqueous phase is extracted twice with diethyl ether
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue is chromatographed over silica gel (mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-13d5041e4c3941b9b642c3c05c5857fd
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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