Water → Methyl 7-(1-hydroxy-2-naphthyl)-5-heptynoate

HRID 703871Notes

Reaction equation

HRID 703871 reaction equation
C(S)C.B(F)(F)F.CCOCC.C([O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH2:31][C:32]#[C:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])C1C=CC=CC=1.O>C(Cl)Cl.CCOCC>[OH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH2:31][C:32]#[C:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38]

Participants

7

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 15617824HCID 15617824, compound

Product 1

HCID 15617825Methyl 7-(1-hydroxy-2-naphthyl)-5-heptynoateYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethanethiol (12.0 mL, 0.162 mole) and boron trifluoride etherate (6.0 mL, 0.049 mole) was stirred at room temperature. A solution of methyl 7-(1-benzyloxy-2-naphthyl)-5-heptynoate (2.05 g. 0.006 mole) in methylene chloride (8 mL) was added and the mixture was stirred for 1.5 hours, then poured into water. The crude product was isolated by extraction with ether, and chromatographed with 2:1 ether/hexane. The title compound (1.09 g, 71%) was obtained as a colorless oil. Mass spectrum: m/z=282.

Workup

  1. customchromatographed with 2:1 ether/hexane

Sources & evidence

ORD record
ord-d7002d2aeb714268bd26bcd32d19152f
Source dataset
uspto-grants-1991_01
Patent number
US04985442

Reaction notes

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