Hydrochloric Acid → (+-)-trans-1-t-Butyldimethylsilyloxymethyl-4-methylene-2-phenylcyclopentane

HRID 1634269Notes

Reaction equation

HRID 1634269 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[Si:15]([O:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@H:4]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 18686190(+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

Product 1

HCID 18686191(+-)-trans-1-t-Butyldimethylsilyloxymethyl-4-methylene-2-phenylcyclopentaneYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+−)-trans-1-hydroxymethyl-4-methylene-2-phenylcyclopentane from Step B (2.5 g, 13.3 mmol) in methylene chloride (50 mL) was added t-butyldimethylsilyl chloride (3.0 g, 20 mmol) and DIPEA (4.7 mL, 27 mmol). The reaction was stirred at rt for 16 h, poured into dilute aq. HCl and extracted twice with ether. The organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (5% ethyl acetate in hexanes) to afford the title product (4.2 g) as a oil.

Workup

  1. extractionextracted twice with ether
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-13e232a3f261468c84c58d772cc5cacf
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Reaction notes

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