Acetone Cyanohydrin → HCID 86630223, compound

HRID 1867643Notes

Reaction equation

HRID 1867643 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:18][CH2:19]O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][O:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)(O)[C:51]#[N:52].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CCOCC>[F:27][C:24]([F:26])([F:25])[C:22]1[CH:21]=[C:5]([CH:4]=[C:3]([C:2]([F:28])([F:29])[F:1])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:18][CH2:19][C:51]#[N:52])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][O:10]1

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57691447HCID 57691447, compound

Product 1

HCID 86630223HCID 86630223, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-1,3-dihydroisobenzofuran-1-yl)ethanol (250 mg, 0.60 mmol) and triphenylphosphine (390 mg, 1.5 mmol) in tetrahydrofuran (2.5 mL) at 0° C. was added acetone cyanohydrin (0.163 mL, 1.8 mmol), followed immediately by the addition of diethyl azodicarboxylate (0.234 mL, 1.5 mmol). The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was diluted with ether, washed with water, then saturated sodium bicarbonate, then water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%-->19% EtOAc/Hex) gave 214 mg (84%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.77 (s, 1H), 7.66 (s, 2H), 7.35 (m, 2H), 7.25 (m, 1H), 7.18 (d, J=6.7 Hz, 1H), 5.14 (s, 2H), 4.64 (s, 2H), 3.65 (s, 2H), 2.38 (m, 2H), 2.22 (m, 1H), 2.07 (m, 1H); 13C-NMR (CDCl3, 126 MHz) δ 140.9, 140.0, 139.4, 131.8 (q, J=33.6 Hz), 128.9, 128.0, 127.2, 123.4 (q, J=273 Hz), 121.7, 121.6, 121.5, 119.7, 88.9, 76.2, 73.1, 72.1, 32.4, 11.8. Mass spec.: 430.09 (MH)+.

Workup

  1. washwashed with water
  2. dry with materialsaturated sodium bicarbonate, then water, then brine, dried over magnesium sulfate
  3. concentrationconcentrated
  4. customColumn chromatography (12%-->19% EtOAc/Hex) gave 214 mg (84%) as a colorless oil

Sources & evidence

ORD record
ord-fc214315509246a7b933d7551953f2ad
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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