Water → HCID 59796272, compound

HRID 1093932Notes

Reaction equation

HRID 1093932 reaction equation
O[CH2:2][CH:3]1[CH2:7][CH:6]([CH2:8][OH:9])[CH:5]=[CH:4]1.[N:10]1C=CC=C[CH:11]=1.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(Cl)Cl>[C:16]([O:9][CH2:8][CH:6]1[CH2:7][CH:3]([CH2:2][C:11]#[N:10])[CH:4]=[CH:5]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6456Trityl chlorideHCID 13239166HCID 13239166, compound

Product 1

HCID 59796272HCID 59796272, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (4-hydroxymethyl-cyclopent-2-enyl)-methanol (13.8 g, 107.81 mmol, prepared by method of Mekrami et al., Tetrahedron: Asymmetry 1992, 3, 431) in methylene chloride (100 mL) was added pyridine (25.5 g, 118.59 mmol) and trityl chloride (33.06 g, 118.59 mmol) at room temperature and the mixture was stirred for 18 h. After addition of water (50 mL), the reaction mixture was diluted with methylene chloride (100 mL) and the organic layer was separated. The aqueous layer was further extracted with methylene chloride (100 mL). The combined organic layers were washed with water (100 mL), brine (50 mL), and dried (MgSO4). After filtration, the filtrate was concentrated and the residue was purified on a silica gel column using ethyl acetate in hexanes (0 to 30%), which afforded 18.25 g (45.7%) of desired product, (4-trityloxymethyl-cyclopent-2-enyl)-methanol.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was further extracted with methylene chloride (100 mL)
  3. washThe combined organic layers were washed with water (100 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-3d8957ac86824a33b05229077631bfed
Source dataset
uspto-grants-2012_03
Patent number
US08133870B2

Reaction notes

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