2-Phenyl-1,3-dithiane → 3-(2-Phenyl-[1,3]dithian-2-ylmethyl)-furan

HRID 604477Notes

Reaction equation

HRID 604477 reaction equation
CC(C)([O-])C.[Na+].C([Li])CCC.[C:12]1([CH:18]2[S:23][CH2:22][CH2:21][CH2:20][S:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br[CH2:25][C:26]1[CH:30]=[CH:29][O:28][CH:27]=1>CCCCCC.C1COCC1>[C:12]1([C:18]2([CH2:25][C:26]3[CH:30]=[CH:29][O:28][CH:27]=3)[S:19][CH2:20][CH2:21][CH2:22][S:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 215472-Phenyl-1,3-dithianeHCID 110949343-(Bromomethyl)furanHCID 23676156Sodium t-butoxideHCID 178418339Butyllithium2×

Product 1

HCID 577096033-(2-Phenyl-[1,3]dithian-2-ylmethyl)-furan

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of sodium tert-butoxide (5.16 g, 54 mmol) in dry hexane (120 mL) was added n-butyl lithium (34 mL, 51 mmol) at 0° C. and stirred for 1 h at 0° C., and then for 1 h at room temperature. The mixture was cooled to −78° C., and transferred to a preformed mixture of 2-phenyl-[1,3]dithiane (10.0 g, 51 mmol) dissolved in dry THF (120 mL) at −78° C., and n-butyl lithium (34 mL, 51 mmol) and kept for 15 min. A dark brown colored solution was observed. After stirring for 1 h at −78° C., 3-bromomethyl-furan (Danso-Danquah R. E. and Scott A. I. Tetrahedron, 1993, 49, 8195-8210; New D. G. et al, J. Org. Chem., 1996, 61, 1578-1598) (10.7 g, 66 mmol) was added via canula. After 30 min., the reaction mixture was quenched with water and warmed to ambient temperature. The reaction mixture was extracted with diethyl ether, and the organic extracts were dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography using 0.2-0.5% ethyl acetate in hexane as eluent. Yield: 5.6 g, 32%.

Workup

  1. waitfor 1 h at room temperature
  2. temperatureThe mixture was cooled to −78° C.
  3. stirringAfter stirring for 1 h at −78° C.
  4. waitAfter 30 min.
  5. customthe reaction mixture was quenched with water
  6. temperaturewarmed to ambient temperature
  7. extractionThe reaction mixture was extracted with diethyl ether
  8. dry with materialthe organic extracts were dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-a8bfcde3e78b4acd831c97da3409b2da
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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