Hexane → [2-(1-Benzenesulfonyl-cyclohex-2-enyl)-ethoxymethyl]-benzene

HRID 1804763Notes

Reaction equation

HRID 1804763 reaction equation
[CH:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Li]CCCC.[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C([CH:34](Br)[CH2:35][O:36][CH2:37]C(Br)CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:10]1([S:7]([C:1]2([CH2:34][CH2:35][O:36][CH2:37][C:23]3[CH:22]=[CH:21][CH:26]=[CH:25][CH:24]=3)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]2)(=[O:8])=[O:9])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 4622731(2-Cyclohexen-1-ylsulfonyl)benzeneHCID 57064374Benzyl 2-bromoethyletherHCID 178418339Butyllithium

Product 1

HCID 59152663[2-(1-Benzenesulfonyl-cyclohex-2-enyl)-ethoxymethyl]-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Cyclohex-2-enesulfonyl-benzene (7) (10 g, 45 mmol) is dissolved in 450 ml of dry THF and cooled down to −20° C. Then 1.6 M BuLi in Hexane (30.9 ml, 49.5 mmol) is added and stirred for 15 min. After addition of benzyl 2-bromoethylether (8.5 ml, 54 mmol) the mixture is stirred for 1 h at 0° C. Then the mixture is evaporated to dryness. The residue is treated with ice/1M HCl and extracted twice with ether. The combined organic layers are dried over Na2SO4 and evaporated under educed pressure. The product is used in the next step without further purification.

Workup

  1. stirringis stirred for 1 h at 0° C
  2. customThen the mixture is evaporated to dryness
  3. additionThe residue is treated with ice/1M HCl
  4. extractionextracted twice with ether
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. customevaporated under educed pressure
  7. customThe product is used in the next step without further purification

Sources & evidence

ORD record
ord-fdbba50777574fc99442d37cf3c29c3a
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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