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

HRID 2301763Notes

Reaction equation

HRID 2301763 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-phenylcyclopentane

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-b1d7c3482069427ba8357d14fad6f7a1
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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