2,2-Dimethoxypropane → HCID 46194819, compound

HRID 709918Notes

Reaction equation

HRID 709918 reaction equation
[OH:1][CH2:2][C:3]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH2:7]1)[CH2:4][OH:5].CO[C:27](OC)([CH3:29])[CH3:28].B(F)(F)F.CCOCC.C(Cl)Cl.CO>C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:3]1([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:4][O:5][C:27]([CH3:29])([CH3:28])[O:1][CH2:2]1)[CH2:15][CH2:14]2

Participants

7

Reactant 4

HCID 64952,2-Dimethoxypropane2×HCID 8000Boron trifluoride etherateHCID 21226129Dichloromethane methanolHCID 86642937HCID 86642937, compound

Product 1

HCID 46194819HCID 46194819, compoundYield 125.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 1,3-dihydroxy-2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-ylcarbamate (0.400 g, 0.00118 mol) was treated with 2,2-dimethoxypropane (20.0 mL, 0.163 mol) and p-toluenesulfonic acid monohydrate (0.0226 g, 0.000118 mol) in ethyl acetate (20.0 mL, 0.205 molat r.t. for 24 hours. The solvent was removed. 2,2-dimethoxypropane (20.0 mL, 0.163 mol) was added, followed by boron trifluoride etherate (0.150 mL, 0.00118 mol). The mixture was stirred at r.t. overnight. The mixture was quenched with saturated NaHCO3 aqueous solution, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated to give a crude. Chromatograph with DCM:MeOH (100:0 to 93:7) gave a solid product (560 mg, 100%). 1H NMR (CHLOROFORM-d) δ: 6.89-6.99 (m, 1H), 6.49-6.65 (m, 2H), 6.46-6.47 (s, br, 1H), 3.99 (m, 4H), 3.13-3.30 (m, 4H), 2.69-2.85 (m, 2H), 2.10-2.39 (m, 1H), 1.56 (s, 6H), 1.37-1.50 (s, br, 9H). MS (M+Na+): 400.0.

Workup

  1. customThe solvent was removed
  2. customThe mixture was quenched with saturated NaHCO3 aqueous solution
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude

Sources & evidence

ORD record
ord-86b5427801374546a9d2a37bf6c48264
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

Loading…