Dichloromethane → HCID 86668414, compound

HRID 713879Notes

Reaction equation

HRID 713879 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([CH2:23][OH:24])[CH:17]=[CH:16]3)[CH2:2]1.C(Cl)Cl>>[CH2:5]1[C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:1][CH2:2][CH:3]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([CH:23]=[O:24])[CH:17]=[CH:16]3)[CH2:4]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 66926446(6-(Spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)methanol

Product 1

HCID 86668414HCID 86668414, compound

Procedure

To [6-(Spiro[5.5]undec-3-yloxy)-naphthalen-2-yl]-methanol (150 mg, 0.46 mmol) in methylene chloride (5 mL, 80 mmol) was added Des-Martin periodinane (0.274 g, 0.647 mmol) and the resulting solution was stirred at room temperature for 1 hour. The crude reaction was then passed through a silica gel plug, the filtrate was removed under vacuum to give 6-(spiro[5.5]undecan-3-yloxy)-2-naphthaldehyde as a colorless solid. (0.150 g, 100%). 1H NMR (400 MHz, CDCl3) δ 10.09 (s, 1H), 8.25 (s, 1H), 7.92-7.89 (m, 2H), 7.78 (d, J=8.7 Hz, 1H), 7.24-7.19 (m, 2H), 4.48 (m, 1H), 1.96-1.29 (m, 18H).

Workup

  1. customThe crude reaction
  2. customthe filtrate was removed under vacuum

Sources & evidence

ORD record
ord-b04f886c2eb74caf8fc72803077b3be6
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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