Water → HCID 15143605, compound

HRID 1084815Notes

Reaction equation

HRID 1084815 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28].O>ClCCl>[CH2:30]([O:29][C:27]([O:18][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:28])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 160268Dup 654

Product 1

HCID 15143605HCID 15143605, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenylmethyl-1-naphthol (5.00 g, 0.021 mol) and triethylamine (2.53 g, 0.025 mol) in dichloromethane (65 mL) was stirred at 0°. Ethyl chloroformate (2.73 g, 0.025 mol) was added and the mixture stirred for one hour at 0°, then for two hours at room temperature. Water was added and the mixture was extracted with dichloromethane. The organic phase was dried over MgSO4 and concentrated. The residue was flash chromatographed (5% ethyl acetate/hexane) to provide the title compound (6.50 g, 100%) as a viscous oil: NMR (CDCl3) 7.84 (t, J=8 Hz, 2H), 7.68 (d, J=7 Hz, IH), 7.50 (m, 2H), 7.25 (m, 6H), 4.30 (q, J=7 Hz, 2H), 4.IO (s, 2H), 1.36 (t, J=7 Hz, 3H); IR (neat) 1760; Mass Spec (EI) 306 (45), 262 (32), 234 (86), 215 (31); Calcd. for C20H18O3 : C-78.40 H-5.92; Found: C-78.49 H-6.06.

Workup

  1. waitfor two hours at room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ed95d69c071b4ef88a657624dbdd16c1
Source dataset
uspto-grants-1991_04
Patent number
US05006555

Reaction notes

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